


Later That Night

by DRHPaints



Category: Conan O’Brien, Late Night Host RPF, Late Night with Conan O’Brien
Genre: Anal Sex, Angst, Conan O’Brien - Freeform, Cunnilingus, Description of F/F Sex, Drug reference, Explicit Language, Explicit Sexual Content, F/M, Face-Sitting, Fluff, Long-Term Relationship, Love, Mention of Bondage, Mention of Slapping, Oral Sex, Public blowjob, Smut, Suicide reference, Unintentional Sex Injuries, alcohol use, blowjob, mention of domestic abuse
Language: English
Status: Completed
Published: 2020-07-14
Updated: 2020-07-14
Packaged: 2021-03-05 02:35:23
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 9
Words: 47,399
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25257016
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: Conan meets an author who comes on his show to promote her book.
Relationships: Bill Hader/Original Female Character, Conan O’Brien/Original Female Character - Relationship
Comments: 2
Kudos: 13





	1. Chapter 1

**Author's Note:**

> This starts around 2008-ish. Please forgive any inaccuracies. Thank you.
> 
> If you enjoy this, please leave a comment or come say hi on Tumblr at fandomtransmandom :-)

“Ten minutes, Ms. Greene,” a gruff voice called through the door. Gwendolyn attempted to shout back a ‘thank you’ but the sound that resonated from her vocal chords was barely above a whisper. Wringing her hands and pacing the room for the 43rd time, she stopped at the rear wall, closed her eyes and breathed deeply, only to be interrupted by a knock on the door.  
“Come in!” She said, managing a decent decibel level this time. Her eyes grew wide as her brain attempted to take in the person who entered. Orange hair, blue suit, and even though she knew ahead of time that he was 6’4” she was still taken aback by how terribly _long_ he seemed.   
“Wow…uh…” Conan said, eyes widening and head twitching to the side in his characteristic manner. “I wasn’t expecting…I mean they said we had an author on today and you’re so…um…”   
Gwendolyn noticed a blush rising on his neck and could feel the heat in her own face as she fought the impulse to fidget.  
Conan looked at the ground for a second and chuckled a bit to himself. “Hi, I’m Conan O’Brien, I put my foot in my mouth in front of beautiful women,” and extended his hand. She laughed harder than she normally would out of nerves and shook it, immediately putting her hands behind her back so he wouldn’t see her anxious fingers dancing about.  
“Well, I just like to come and introduce myself before the show, see if you need anything.”  
Gwendolyn nodded. “Oh, that’s sweet of you, thank you. No, I’m okay. A producer came by earlier and I gave him a picture that we can talk about on the air. Should be pretty funny…” She realized she was babbling and bit her cheek. _Breathe Gwen, Breathe._  
“Well, alright there,” Conan said, affecting an old-timey accent that made Gwendolyn giggle. “I’ll see you out there, ready and raring to go!” Leaving her laughing, he strolled out of the room. Taking one last look in the mirror Gwendolyn touched up her lipstick and did some deep breathing. _Here goes nothing._

***

“Now our next guest is a New York Times best-selling author and she recently won the Hugo Award for her novel, “The Dragon’s Hide Curse.” Please welcome, Gwendolyn Greene!”  
Gwendolyn walked out to the cheers of the audience and the barrage of lights and cameras, silently thanking every deity in existence for making it to the chairs without tripping and falling on her face. She hugged Andy and then Conan, whom she couldn’t help but notice smelled extremely good, and sat down, folding her hands and willing them to sit still.  
“Hello, Gwendolyn, thank you for coming.”  
“Thank you so much for having me, Conan, this is a dream come true. I’ve been a huge fan of yours since your very first show and it’s an honor to be here.”  
“Oh that’s very nice of you to say,” he paused. “Now my producer Jeff Ross tells me you might have been a little more than a fan, tell us about that.”  
“Well, it’s a little embarrassing, Conan,” Gwendolyn covered her face for a moment, “but I had a bit of a crush on you in college. I gave Jeff a photo if you want to see…and…well…”  
The crowd woo’s and Conan says, “Well, well, well,” as a photo is shown of a young, curly-haired Gwendolyn kissing a poster of Conan’s _Rolling Stone_ cover from 1996.  
Gwendolyn laughs and covers her ever-reddening face. “My friends made fun of me for it quite a bit.”  
“Now wait a minute here,” Conan said, pausing for laughter. “I don’t understand what’s funny…about a beautiful woman…being attracted…to all… _this_.” Conan gestured salaciously to his own body.  
“Well, you see my friends had fellows like Leonardo DiCaprio, Brad Pitt, George Clooney...and there I was rocking the Conan poster,” Gwendolyn said with a chuckle. “Personally I think I have excellent taste.”  
Conan laughed, “Or you’re mildly delusional, not that I mind. Anyway, we should probably discuss your book. “The Dragon’s Hide Curse,” it’s become a phenomenon, I can’t go anywhere without hearing about this thing. What is this like for you having this become such a hit overnight?”  
“Oh it’s mind-boggling. I mean just a couple of years ago these characters were just people inside my head, and now people are dressing up in costumes and naming their babies after them, it’s truly unbelievable.”  
“Wow, that’s amazing. Congratulations. Now, the question everyone wants to know. When is the sequel coming out? People are desperate for this thing.”  
“Well, if all goes well, and so far it is, it should be out early next year.” The crowd cheered and Gwendolyn pressed her hands to her cheeks in gratitude.   
“Very exciting, thank you so much for being on the show. Your book, “The Dragon’s Hide Curse” available absolutely everywhere, Gwendolyn Greene everybody, thank you, we’ll be right back!”  
Conan leaned over and placed his hand lightly on Gwendolyn’s shoulder. “Nice job, very funny.” Their eyes locked for a moment and she barely had time to utter a breathy thank you before she was ushered back to her dressing room by someone in a head set.   
Collapsing onto the couch, she pressed a hand to her chest and breathed into it. _I made it through_ , she thought. She’d been panicked about making a fool of herself and all in all it had gone better than expected. She changed back into her t-shirt and cut-off shorts, zipping her fancy dress into its plastic bag and doing a once over of the room to make sure she hadn’t left anything behind when she heard a knock at the door.   
“Come in,” she said, amazed at how calm her voice was now compared to before the show.  
Conan strolled in, still in his blue suit, but his tie was pulled loose. Gwendolyn felt a rod of anxiety stiffen in her spine, and wished she was still in the armor of her sexier dress instead of her schlubby t-shirt and jean shorts.   
“Hey, uh, I just wanted to see how you were doing and thank you again for coming on the show,” he said, shifting his weight back and forth a little too quickly.   
It was then that Gwendolyn realized, _He’s just as nervous as I am._  
“Oh it was so great, thank you. I was very anxious and you really helped me out there. I’ve never done a tv interview before but when my agent said I had the chance to be on your show I couldn’t turn it down.”  
Conan smiled and rubbed the back of his head. “Well, I’m really glad you decided to come, and, um, I hope you’ll come back when your next book comes out.”  
“Oh definitely. If you’ll have me.”   
Their eyes met for a moment and they were silent before Conan extended his arms and said “Well, thanks again.” They hugged and both of them seemed to linger a little longer than necessary.   
When they parted Conan’s eyes darted about quickly and he said, “Well, goodbye then,” and opened the door to leave. Gwendolyn said goodbye, but Conan took one step out into the hallway and froze, hand on the doorframe. He made a fist, pounded it twice, and turned around.  
“You know, um…I mean I know this is…I know you came here in a professional capacity and maybe this is…It might not be…but I just know I’d regret it,” He screwed up his face and shook his head before looking Gwendolyn directly in the eye. “What I’m trying to say is, could I take you to dinner sometime?”  
Gwendolyn could see her own expression reflected back at her in the mirror to her right and she did not know her own eyes could go that wide. For a moment she thought she might be having some kind of psychotic break because surely Conan O’Brien did not just ask her to dinner, and surely he was not nervous about doing so. After all of this ran through her mind she realized she had not answered and the poor man was still waiting for a response.  
“Y-yes, I-I’d like that very much,” she desperately tried to maintain some sense of composure and prayed that he wasn’t looking at her hands, which betrayed her by violently shaking.  
“Great,” he exhaled, smiling. She gave him her number, and told him to call anytime, kicking herself internally because she thought that might sound too eager. He left with a little wave and she closed the door, immediately sinking to the floor, letting out a huge breath she wasn’t aware she’d been holding. 

  
Conan called two days later and they set up a date for that Friday. As Gwendolyn got ready she regretted not asking for more details about where they were going so she knew how formal to dress. What if he took her somewhere with all of his famous friends and she stood out for being shabby? Finally she settled on a form-fitting purple sun dress that complimented her auburn hair and green eyes, and wouldn’t look like she was trying too hard if he took her somewhere casual.   
The doorbell rang and Gwendolyn did a quick look in the mirror before rushing downstairs. Taking one deep breath she relaxed her face and opened the door. Conan stood there smiling in a blue button-up shirt and dark wash jeans. She’d hardly seen him in casual wear before and instantly found it sexy.  
“Hi, wow, you look gorgeous,” he said, leaning in for a quick hug.   
“Thank you, you too. I love this look,” she said, rubbing the lapel of his shirt between her fingers. Conan chuckled and they walked down the steps.   
“I was thinking we could go to this little Korean place I know not far from here. You like Korean? It’s really good. I go there all the time…” She wanted to tell him that sounded great but he was talking faster and faster, gesturing wildly with his hands, and she couldn’t get a word in. Worst of all, she found she couldn’t keep up with his long-legged strides, particularly in the heels she immediately regretted wearing.   
“Conan. Conan!” She grabbed his shoulder and turned him around.  
“Wha-?” He started to say, but before he could finish she leaned in and kissed him. Slowly. Patiently. Her hands snaked up his shoulders and into his orange pompadour, rubbing the back of his neck. Feeling his shoulders loosen and his arms wrap around her waist as their tongues slowly intertwined, the cacophony of the New York street became fuzzy and the looks of passersby were of no consequence as they sunk into one another and their breath began to sync, rising and falling against one another on the sidewalk.  
Gwendolyn pulled away reluctantly, eyes opening. “Why, um…what was that for?” Conan said, arms still around her, thumbs making small circles at her waist.  
“I thought maybe if we got that out of the way maybe we’d both be less…nervous and we could just have a good time.”   
Conan nodded and let out a breath. “Good. Good idea.”  
“Also, I just really, really wanted to.” Gwendolyn shrugged her shoulders and Conan chuckled a bit.   
They proceeded on their way, Conan’s hand on the small of her back as he walked at a more reasonable pace. A few people stopped him and asked for autographs and every time he was cordial and polite. A group of guys yelled out “CONAN!” And he gave them an exuberant wave. It was obvious he’d accepted the fact that he couldn’t go without being noticed, but he still apologized to Gwendolyn every time for it interrupting their date no matter how much she said she didn’t mind.  
When they reached the restaurant he was warmly greeted by the proprietor and they were ushered to a corner booth that faced away from the windows. “Your usual, Mr. Conan?” the hunched, elderly Korean gentlemen said with a wide smile.  
“I think we’ll need a minute, thank you, Kwan,” Conan smiled and Kwan nodded, leaving them to peruse the menu. “The bulgogi is excellent,” Conan said, “I don’t know if you’ve tried it before but it’s…”  
“Yeah, actually, two of my cousins are adopted from Korea and I had a Korean roommate in college who taught me how to make bulgogi. It’s my absolute favorite. I can’t believe I’ve never heard of this place.”  
“Oh really? So you like to cook?” Conan said, taking a sip of water.  
Gwendolyn nodded. “I love it. It’s so…meditative. I find it really calms me down after a long day.”  
Conan shook his head in bewilderment. “That must be because you’re good at it,” he chuckled. “There’s nothing “meditative” about burning your fingers and starting several small fires.”  
Gwendolyn laughed. “I take it you don’t cook then?”  
“Uh…no. The best I could do is make you my famous toasted pop-tart.”  
They were laughing when Kwan reappeared and Conan placed their order, adding a couple of appetizers to share. Kwan graciously took their menus and receded, and Conan turned back to her with a smile.  
“So as a writer you must get to make your own schedule pretty much, right? That must be nice.”  
“Yeah,” Gwendolyn replied, “I mean I have to do a lot of promotional stuff that I don’t really care for. Book signings, public readings-“  
“Talk shows?” Conan suggested with a sly smile.  
“Well,” she said with a smile, “As excited as I was to come on the show I have to admit I was equal parts terrified. Public speaking doesn’t come easily to me and I’d be lying if I said I didn’t find you more than a little…intimidating.”  
“ _Me_?” Conan said, with over-exaggerated shock. “ _Intimidating_? I never!”  
Gwendolyn laughed. “I mean I didn’t know what to expect. Certainly not this.”  
“Well, I’m glad you took the risk,” Conan smiled.  
“Me too,” she responded. “How about you? Your schedule must be crazy with the show and everything. I admit I was surprised that you called me so soon.”  
“Yeah we film Monday through Friday and I often have various obligations that keep me busy on the weekends, but I was lucky enough to get some time free this week.”  
“How do you spend your free time?” She asked.  
“Oh you know, fiddle around with the guitar, as much reading as I can. Speaking of, I started your book the other night and I have a bone to pick with you,” he said, pointing at her accusingly.  
Gwendolyn was taken aback. “Y-you do?”  
“Yes. It’s absolutely fantastic and I could not put it down. I didn’t get to sleep until two in the morning and I was useless the next day on set and it’s completely your fault.”  
Gwendolyn laughed and clutched her chest. “Whew, you had me worried there. I’m glad you’re enjoying it.”  
“Yeah, fantasy isn’t typically my thing if I’m honest, but I love how dark and gritty it is and—,” he leaned in close to her and lowered his voice. “It’s surprisingly sexy, which I did not expect at all.”  
A sly smile crossed Gwendolyn’s face. “Yeah, well, one of my gripes with the fantasy genre is that it’s often too high-minded and removed from reality. I think we can have elements of the fantastic and still incorporate the realism of humanity. And that, of course, includes…sex.” She willed herself not to fidget or bite her lips but could tell she was losing the battle.  
“The way you write it is very…provocative. Particularly that first scene between Seasnan and Cassandra I mean…wow.” He flicked his eyes up at her and his tongue darted to the corner of his mouth. She was almost positive he was unaware of this behavior, but it was making her squirm all the same.  
“Thanks, I do my best,” she replied with a half shrug. They were quiet for a moment, both looking down at their hands as if their own nervous movements were suddenly fascinating.  
Conan cleared his throat after a moment. “So how long have you been in New York?”  
“Only about a year actually,” Gwendolyn exhaled in relief. “Once the book hit the market and did better than anyone could’ve predicted I decided to just go for it and move out here. Before that I was living in a small suburb of Minneapolis.”  
“Ah! That’s it! Ive been trying to place your accent this whole time!” Conan said, thumping his fist on the table.  
“Oh no, don’t tell me I sound like one of the characters from _Fargo_ and I can’t hear it?” Gwendolyn cringed.  
“No, not that bad,” Conan laughed. “But you certainly have that midwestern cadence. Especially with your ‘O’s’”  
“Ugh, I know, it’s a dead giveaway,” Gwendolyn shook her head. “Speaking of, how did you get rid of your accent? You’re from Massachusetts, right? Did you have to practice a lot?”  
Conan chuckled. “Yeah, luckily I never had that terribly heavy _Bahhhston_ accent, growing up in Brookline, but every now and then I’ll catch myself saying a word or two particularly after a visit back home, and I can really hear it.”  
“Do you get back home often?”  
Conan shrugged. “Not as much as I would like, and certainly not as much as my mother would like, but I try. How about you, what’s your family like?”  
Gwendolyn pulled back and cricked her neck. “Well my family…they’re…they don’t make for pleasant dinner conversation.”  
“Oh I’m…sorry, I didn’t—“  
“No, it’s fine, it’s just…it’s a story for another day.”  
“No problem,” Conan nodded. “So aside from writing, how have you been spending your first year in the city?”  
“Well, I spend a lot of time making art. Drawing, painting, stuff like that. I also really love to go out dancing.”  
“Dancing? Really?”  
Just then the food arrived. They thanked Kwan and dug in, enjoying the delicious offerings and remarking on the quality.  
“So you like to dance?” Conan prompted, wrapping his mouth around a pork bun.  
“Oh I love it,” Gwendolyn said after swallowing. “In fact, did you have something planned after dinner?” She asked, eyebrow raised.  
Conan looked at her for a moment before waving his hand and shaking his head. “No. No, no, no. You do not want to see me dance. I look like Gumby having a seizure.”  
“Oh, come on,” Gwendolyn chuckled. “I bet you’re better than you think. And I know a great club only a couple of blocks from here. Plus,” she said, pointing her fork at him. “I can almost guarantee practically no one there will recognize you. Let’s just say it’s probably not your…demographic.”  
Conan tapped the table in contemplation. “Alright, we can go. But on one condition,” he held up a finger. “And that is that once you see me dance you must promise, promise, that you will still be attracted enough to me after to want a second date.”  
Gwendolyn threw her head back and laughed. “Alright, I swear. If anything the fact that you’re willing to try will make you more attractive.”  
“Well, alright then,” Conan responded with a smile.  
They finished their meal, paid, and left. Gwendolyn directed them a couple of blocks away to what Conan noticed was a considerably rougher neighborhood than he was used to occupying. He could hear the bass pounding before they turned the corner and they came upon a rusty railing bedecked with an overhang marked “Reggie’s.” An absolute monster of a man stood out front. Conan wasn’t used to feeling short but this guy made him look positively petite.   
But as soon as he saw Gwendolyn he opened his bear arms wide for a hug. “Hey girl, haven’t seen you in a while, what’s up?”  
She ran up and kissed him on the cheek. “Hey Bruce, how’s the crowd tonight?”  
“Oh it’s hot. You’ll love it. Who’s the string bean?” He asked, looking Conan up and down.  
Gwendolyn gave him a loving punch that made no impact on this mountain of a man. “Be nice. This is my date, Conan.”  
“Can this boy dance?” Bruce asked, eyebrow raised.  
“If not, he’s going to learn tonight,” Gwendolyn said with a little shimmy.  
“Oh ho! He sure is. Have fun in there. See ya later.” Bruce ushered them in and Gwendolyn grabbed Conan’s hand.   
The doors opened immediately to a staircase and she led him down through a pulsating mass of people. Conan could feel the music vibrating up through his feet though he was certain he’d never heard the song before. Gwendolyn crooked a finger at him and pulled the front of his shirt, guiding him to the dance floor.  
Before he knew what was happening she was undulating before him, her body moving as if it were made of flowing fabric. He didn’t know what to do, but she took his hands and placed them on her hips, and her fingers crawled up his chest, caressing his neck, before working their way into the base of his neck where they gently rubbed in time to the music. Her body moved into his, then out again, pressing and releasing in an addictive rhythm that it took him a while to become acclimated to, but once he did he found that he could mirror her, at least in a somewhat jerky manner. Gwendolyn turned around, reaching up to encircle his neck with her arms and ground her ass into him. Moving his hips in a circle Conan followed her lead, burying his face in the crook of her neck, gently pressing a kiss into the hollow.  
The next song that came on was slower. Gwendolyn turned around and pressed herself against him, writhing back and forth as they paced beneath the pulsing lights of the club. They looked at one another intensely, breathing hard through their mouths, not wanting to break eye contact. Gwendolyn began to nuzzle him, pressing her face into his neck, even reaching up to take a nip at his earlobe.  
As the song died she pressed her lips to his ear, “Want to get out of here?”  
“Yes,” Conan said breathlessly.  
Gwendolyn nodded and took his hand, leading him back up the stairs and out into the night air which now felt incredibly refreshing and crisp. She immediately strode forth and hailed a cab.   
Conan climbed in after her. “Just one stop,” she said to the driver before turning to Conan. “You want to give him your address?” Or should I give him mine?”  
Conan attempted to hide the tremble in his voice as he squeaked out his address and failed, badly. Gwendolyn placed her hand on his thigh and was rotating her thumb in tiny circles. Conan could feel his heart beating a tattoo against his chest as he saw the city whip by outside the windows and barely registered the cab driver yelling at a passing car.  
They pulled up outside of his building and jumped out. Conan fumbled with his keys and dropped them on the way to the door. Gwendolyn placed a hand on his back and he could feel every single point of contact as the key slid home, swinging the door open.  
They walked up the stairs and went inside Conan’s apartment. “So, uh, here it is. Been here for a few years. I like it, it’s pretty nice. Here’s the kitchen, and there’s a study and…and…” Conan had been gesturing to and fro as he walked into the apartment and when he turned around to look back, Gwendolyn was stepping out of her purple dress and slowly walking toward him in a black lace bra and underwear.  
“Wow, I, um…” he began, but she didn’t let him finish. She reached up and kissed him, her fingers flying down the buttons of his shirt as their mouths quickened in rhythm. Conan buried one hand in her wavy red hair while the other rested nervously at her waist. She pulled off his shirt and walked him backwards slowly.  
“Bedroom?” she asked, looking into his crystalline blue eyes. Conan nodded and led the way. Gwendolyn reached down and took off her heels as she followed. They stood at the foot of the bed and she ran her fingers over his sparse orange chest hair before leaning in to kiss him again. Gwendolyn reached down and slowly began to undo the button and zipper of his jeans, and he slithered out of them, keeping his boxers on. Gwendolyn reached back and unhooked her bra, dropping it on the floor. Conan stared at her for a moment and she guided his hand to her breast. He began to caress her, running his long fingers gently over her nipples. Gwendolyn took a step back and slowly worked her underwear down her hips, stepping out of them before moving to the bed and laying down. She looked up at Conan who hesitated for a moment before hooking his thumbs beneath the waistband of his boxers and unceremoniously removing them. He was mostly erect and Gwendolyn was pleasantly surprised to see that all his jokes about his manhood on the show over the years hadn’t been based in fact.  
He joined her on the bed and they kissed, melting into one another as they languorously ran their hands over one another. Conan inched his fingers down her abdomen and slowly slid his hand between her legs, petting the lips of her sex gently for a few moments before sliding a single finger into the wetness that resided there. With aching patience he began circling and stroking her clit, teasing her with differing pressures before adding a second finger, all the while kissing her and keeping his other hand ensconced in her hair.Gwendolyn reached down and ran her fingers down the length of his cock, stroking upward and encircling it in her warm palm, pumping up and down slowly. Conan, however, moved her hand away and she took the hint that he didn’t want to become overexcited just yet.  
He pulled back and stared at her for a moment. Gwendolyn was already breathing hard and looked back at him, her emerald eyes darting back and forth between his own. He leaned forward and kissed the crook of her neck, slowly working his way down her body, stopping to massage her breasts with his agile fingers before making it down to her thighs. He kissed them, biting the inside tenderly, before pressing his lips against hers and spreading her with his fingers. Conan began licking in slow, wide circles, making them tighter and tighter until his tongue was wrapping its way around her now-engorged clitoris. Gwendolyn moaned and ground herself against him, dripping wet against his face as he began to lightly suck on her clit. She bunched her hands in the sheets and her heels dug into the bed as her hips swiveled faster and faster against his eager jaw, her moaning rising in pitch as she approached orgasm. Grasping her hips and pulling her toward him, Conan dug forward, sucking hard and Gwendolyn called out his name, body shaking and writhing under his hands as she fell back onto the bed in a state of ecstasy.  
Conan backed off for a moment and let her breathe, gently rubbing her opening with the backs of his fingers as he waited for her trembling to cease. When her chest began to rise and fall normally again, Conan took two fingers and slid them inside of her, diving back in, licking her feverishly as his fingers pulsed inside of her, crooking his fingertips to find that special spot. In one instant her body rose almost completely off the bed, only her feet and head remained, and immediately he knew he’d been successful. Using his free hand he guided her back down, and she began helplessly thrusting herself into his face as she shouted his name in between a series of expletives. At this point her fingers were pulling on his hair with such ferocity it was almost painful, but he knew she was close and he wasn’t about to stop. He could feel the tremor building inside her and he increased his ministrations, pulsing faster and licking intensely until the quaking overtook her and the aftershocks rocked her body, leaving her quivering and breathless as Conan slowly kissed his way back up to her face.  
Gwendolyn’s breath was shaky and she had both hands over her eyes. “You okay?” Conan asked.   
She peeled away her hands and looked at him, quiet for a few seconds. “Yeah, I just…wow. Wow.”  
Conan shrugged and smiled a little. She smiled back. He turned and rifled through the bedside drawer, coming up with a condom, opening it and rolling it down the length of himself. Climbing on top of her, he stopped for a moment and looked at her, brushing the hair from her face. “Okay?”  
She nodded and rubbed her thumb against his cheek. Conan looked down between them and slid himself into her. Gwendolyn gasped a little and Conan let out a low moan. He held himself there, getting used to the sensation of the pressure for a moment before withdrawing slowly and thrusting again.  
It didn’t take long for them to develop a rhythm, once they did Conan slid one hand between them and used his fingers to massage her clit in time with his strokes, which he noticed greatly increased the enthusiasm of her thrusts. They kissed wildly, but soon were simply breathing heavily into one another’s open mouths as they moaned and called out each other’s names. Gwendolyn’s hips began to work into him with increased speed and she climaxed, clenching around him from the inside and nearly sending him over the edge, but he held on. Calling her name, he began losing control, movements becoming erratic and barely able to draw breath. Finally he heard her yell his name and tighten around him and he gave in, shooting into her with abandon, each cascade of his orgasm throwing them closer together as their bodies collapsed.  
When it was all over they lay there holding one another, breathing hard and slowly rocking back and forth. Conan knew he should withdraw and climb off of her, but it felt so good to be inside of her that he didn’t want to let the feeling go. He slid his arms underneath her and tucked his head into her neck, and Gwendolyn wrapped her arms around him so that they formed a ball of sweaty, limp limbs. They held each other for what seemed like a long time, before finally unraveling and collapsing back onto the bed, naked and flushed.   
Gwendolyn turned her head and looked at Conan. They stared at each other for a moment before they both inexplicably burst out laughing. Then they found they couldn’t stop.  
“I don’t know what’s funny!” Gwendolyn gasped when the laughter finally died down.  
“Me neither,” Conan said, stifling a final chuckle. “Woo, that was fun though.”   
“It sure was. And seriously. Good job. I mean… _seriously_ good. Damn.”  
That got Conan laughing again and it was a couple of minutes before he could stop.  
“I guess…thank you?”  
“No, thank you!” Gwendolyn laughed and Conan grabbed her and kissed her temple. They snuggled up together, getting comfortable under the blankets. Gwendolyn fell asleep first and Conan spent a long time listening to her breathing as the summer moonlight poured in the apartment windows. As he began to drift he noticed a new scent on his sheets. Grapefruit, sweet pea, and something else uniquely her. _Gwendolyn_.

  
Gwendolyn woke first in the morning and crept quietly to the bathroom. Glad she had succeeded in not waking Conan, she slid back into bed and couldn’t help but notice his half-hard cock under the sheets. She looked up at his serene, pale face and smirked. Slowly she peeled back the sheet, stopping every so often, worried he’d wake. When finally she exposed his lower half she delicately ran one finger around the head of his penis, looking at his face. His lips perhaps twitched, a little, but he was still out. Deciding to risk it she bent down and took the tip into her mouth, holding it there for a second, allowing him to get used to the warmth before rotating her tongue around the head. Tenderly she began to suck the tip, not moving her head and holding the shaft up ever-so-lightly away from his body. Gwendolyn felt him grow rigid between her lips and cautiously took him down further. A half-groan escaped Conan’s closed lips and she pulled off for a second to look at his face. Still fast asleep. Resuming her pose, she slid down the entirety of his length this time and Conan began to moan in his sleep almost immediately. His hips rocked to meet her mouth and after a couple of minutes she heard a snort followed by, “Wha—? Oh my _fuck_ …” and Conan’s fingers were running through her hair as he let out a deep, satisfied sound.  
She gave up all pretense and used one hand to cradle his balls while the other stroked the shaft, her mouth working the tip of his cock, sucking hard and bobbing up and down in time with her fist. Conan dug his heels into the bed and called her name, gently pushing her head to indicate his preferred speed. “Fuck I’m gonna cum,” he groaned, now openly thrusting into her mouth. She hummed around his cock to indicate her assent and slid all the way down, feeling his hot cum shoot down the base of her throat as he rocked back and forth calling out, “Fuck, Gwen, FUCK!.”   
He took his hands away and she came up, gasping. “I’m sorry,” Conan panted. “I didn’t mean to do that. I mean, I feel bad if you think I was like…making you…”  
“No, not at all!” Gwendolyn said, shaking her head. “Maybe it’s a little…I don’t know…but it really kind of…makes me hot when you, you know, do it like that.”  
“…Really?” Conan asked, eyebrow raised.  
“Yeah, I mean…when you’re moaning like that and losing control and um…well…” Gwendolyn got quiet “Uhh…fucking my face…I kind of love that…” She shrugged and held out her hands and made a “what’re-you-gonna-do” expression.  
Conan chuckled. “Well…alright then. I guess…I guess that’s all…yeah. Well.”  
Gwendolyn laughed nervously, but Conan leaned in and kissed her and her shoulders dropped. “So, what do you have planned for today?” He asked as he stood up and pulled on a fresh pair of boxers.  
“Are you free?” He didn’t look at her as he asked and there was a note of timidity to his voice.  
“Yeah, actually I’m free all day. I have a book signing tomorrow afternoon, but today I’m wide open. Did you want to hang out?” Gwendolyn asked, hooking up her bra.  
“Definitely,” Conan said, leaning in to kiss her forehead before reaching into the closet and pulling out a baseball t-shirt. “Though, like a stereotypical bachelor, I have zero food here, so we’ll have to go out to find sustenance.”  
“Fair enough. Can we swing by my place first? I’d like to shower and get some fresh clothes.”  
“Sure,” Conan said. “I’m going to jump in the shower then while we’re here, do you mind?”   
Gwendolyn shook her head and Conan disappeared to the bathroom. While he was away she took the liberty of peering around the apartment. Though sparse, the décor it did have was tasteful for a bachelor his age, and Gwendolyn was pleasantly surprised. She came upon Conan’s study and saw two guitars, one mounted on the wall. Making a mental note to ask him to play for her someday, she walked to the kitchen and looked through the cupboards. The man really had hardly anything edible to speak of. _No wonder he’s so thin._ She thought, closing the bare refrigerator. Gwendolyn heard the water stop in the shower and figured she should at least look like she hadn’t been creeping around his apartment, so she sat on the bed and waited for him to emerge.  
Conan came out, orange hair wet and slick, which was disarming as she was used to it’s extremely fluffy nature. “Ready?” he asked. She nodded and they headed out the door, luckily catching the first cab that came around the corner.   
As they pulled up to her building Gwendolyn was desperately trying to remember what kind of state she’d left her place in. God forbid she left a vibrator chilling in the bathroom or something. “Well, here it is,” she said, showing Conan around. “This is my office-slash-studio.” She ushered him into a room with an easel bearing a half-finished portrait of a young man and walls bedecked with paintings, and a corner with a laptop and various writing accoutrements.   
“Wow, did you paint all these?” Conan asked, peering around.  
“Yeah, it’s something I picked up a few years ago. I enjoy it. You know what? You should pose for me sometime,” Gwendolyn poked him teasingly.  
“Oh, no, no, no,” Conan said, waving his hands in front of himself. “Absolutely not, I see your game. Have sex with me, get me comfortable, then all of a sudden you’re tricking me into posing nude. Not this guy!” He waggled his thumb in front of his chest.  
Gwendolyn laughed. “Well, maybe I’ll be able to convince you one day,” Conan shook his head and laughed. “I’m going to jump in the shower. Make yourself comfortable and I’ll be out soon.” Gwendolyn went into the bathroom and closed the door. Conan peered around at the paintings, wondering if they were painted from life. Half of them were nudes, both men and women, and he couldn’t help but notice that they were all quite attractive people. He looked over her desk and smiled at her organization, admiring that everything had its place. Looking in the living room, her office, her bedroom, there was one constant: books. She had bookshelves everywhere. And it seemed she read a little of everything. The kitchen was particularly impressive. She had the spices in little magnetic jars stuck to the side of the fridge. Conan had to admit he didn’t know what half of the spices were and he certainly didn’t know how to use a damn one of them, but it made him smile that she did. And even in the kitchen there was a small stack of books, recipe books, of course, and one little journal. After a moment’s trepidation that perhaps this was going too far in snooping, he opened it, only to find that she was working out her own recipes. Her handwriting was pretty without being pretentious and he could see her little notes and corrections as she worked on perfecting her own dishes. Conan smiled and hoped he’d get to taste them someday.   
Just then he heard a door open and quickly shoved the little journal back in its place before Gwendolyn appeared around the corner, hair wet and sporting a green t-shirt and jeans. “So you want to get some breakfast?” Conan asked.  
“We can if you want,” she said with a shrug. “Or I can make something if you want to stay in.”  
She came around the kitchen island and peered in the fridge. “Eggs, bacon, and toast? Nothing fancy but I can whip it up no problem.”  
“You sure? I don’t want you to go to any trouble…”  
“Oh it’s no trouble! In case you haven’t noticed, I enjoy cooking just a little.”  
Conan chuckled and sat across from her, watching as she fried bacon and cracked eggs, seeming to dance around the kitchen, whipping and flipping and toasting, and soon there was a plate of hot food in front of him and Gwendolyn was smiling in the next seat. He took a bite of the eggs and just stared at her for a second. “Alright, what the hell,” he said, looking down at the plate with utter bewilderment. Gwendolyn’s face fell and her mouth turned downward into a frown. “Seriously, these are just eggs. How are they so good?”  
Gwendolyn laughed in relief. “I’m glad you like them. I like to put a little garlic, dill, and celery salt in them. Sometimes I’ll do Sriracha on top too because I like the heat, but I didn’t know how you feel about spicy foods.”  
“I weep from mild salsa, so probably best to avoid that,” Conan said around a muffled mouthful. “But I could eat this everyday.”  
Gwendolyn kissed him on the cheek and turned back to her plate. They finished their meal in silence and afterward Conan leaned back and patted his little belly. “I have a feeling you are going to be responsible for me not fitting in my suits anymore.”  
“Well, to be fair I’ll be helping you work it off,” she raised an eyebrow and Conan leaned in to kiss her.  
Gwendolyn found herself forgetting about the dishes as the kissing intensified, Conan pulling her close. She notched herself between his legs and ran her hands up his arms, burying them in his orange hair.  
“Want to show me your bedroom?” Conan said in a low voice. Gwendolyn smiled and nodded, leading the way, pulling off her shirt as she went. She kicked off her jeans and Conan followed suit, jumping into the bed after her and pulling down her underwear as she unhooked her bra. He kissed his way up her legs, stopping between them and spreading her apart with his fingers, pleasantly surprised with how wet she was already. He began gently lapping at her clit, teasing and encircling it, kissing and sucking it. Thrusting two fingers inside of her, he used his lips and tongue to bring her to panting, shuddering orgasm before kissing his way up her body and massaging her breasts.  
“Condom?” he asked. She nodded and reached into her bedside drawer, rooting around for a moment before retrieving one. Conan let her apply it and she pressed his back into the bed, climbing on top of him. Gwendolyn positioned herself over his cock and lowered herself over him, closing her eyes and opening her mouth in a silent gasp as he entered her. She began to lift and lower herself slowly, rocking her hips back and forth while Conan slid his hand between them to stimulate her clitoris.   
Gwendolyn reached back to balance her hands on Conan’s knees as she began pounding him harder and harder into herself, getting the angle just right and moaning each time his cock hit home. Conan thrust into her, loving the sensation of her body clenching around him with each wave of her hips as he held her. Then Gwendolyn leaned forward, riding him faster, calling out his name as her hair danced in front of him. Conan sat up to better fill her with himself, their faces close, eyes staring into one another as the approaching avalanche of their orgasm threatened to overwhelm them. They both hit the precipice at the same time, jumping with one another’s names on their lips, clutching each other as if they were about to fall into nothingness.  
After breathing into one another for a while they separated and flopped back onto the bed. “I don’t know why I bothered getting dressed,” Gwendolyn said with a laugh.  
“Honestly, if it were up to me you’d be naked all the time,” Conan replied. She playfully punched him and began searching the floor for her underthings. They both got dressed and made their way to the living room, sitting down on the couch. Gwendolyn flipped on the tv and exclaimed, “Ooh, “Magnolia” is on.”   
“You like that movie?” Conan asked.  
“Yeah one of my favorites. I like anything by Paul Thomas Anderson, really.”  
“Great,” he said putting an arm around her. They sat and watched in silence, and after about half an hour Gwendolyn noticed Conan had fallen asleep. She unwound his arm from her shoulder and crept to her studio, grabbing a sketchbook and a few pencils. He looked peaceful and remarkably beautiful when he slept and she began to draw, curled up on the other end of the couch, doing her best not to disturb him. After an hour or so when she was satisfied with the likeness she captured, she again snuggled up next to him and pulled his arm over her. Unfortunately he woke with a start.  
“Oh, sorry, I didn’t mean to fall asleep,” he said groggily, rubbing his face.  
“Don’t worry about it.”  
“Wait a second, is that me?” Conan asked, leaning over and picking up the drawing pad. Gwendolyn meant to put it away but she’d left it open.   
“Yeah…sorry. You just looked so lovely. I couldn’t resist.”  
“This is really good…” Conan said, looking it over. “Can I keep this?”  
“Sure, if you want to,” Gwendolyn shrugged, a small blush rising on her cheeks.  
“Will you sign it for me? I’ll hang it in my office at work.”  
She nodded and scrawled her name in the bottom corner before handing it back to him. He leaned down and gave her a quick kiss on the cheek. “Thank you. I really appreciate it. Now, I don’t know about you but I’m about ready for lunch. Wanna go out? I don’t want to make you cook again.”  
“You’re not making me. We’re not Amish. I legitimately enjoy cooking. But fine, if you want, there’s actually a pretty decent diner around the corner if you’re interested,” Gwendolyn said with a smile.  
“Yeah, that sounds like a plan,” Conan said, standing up and stretching. Gwendolyn gathered up her purse and they headed out the door. Immediately Conan was stopped by an extremely nervous young woman asking for an autograph and a photo and he kindly obliged. Gwendolyn looked on with admiration at how he treated her and made her comfortable in the interaction. They made it to the restaurant without any other interruptions and sat down to order. The waiter said, “Hey, love your show, man!” but beyond that they were left alone.  
“So, did you always want to be a writer?” Conan asked as his sandwich arrived.  
Gwendolyn shook the ketchup out next to her fries. “Well, actually as much as I’ve always loved writing, I tried quite a few other things first. I originally went to school to be a funeral director.”  
“A funeral director?!” Conan said, exasperated.  
“Yeah,” Gwendolyn chuckled. “I have a lot of empathy for people dealing with grief and it seemed like a smart choice. You have job security, it often comes with housing…but I couldn’t hack the chemistry involved.”  
“Wow, yeah, I’m glad you chose writing,” Conan took a big bite.  
“Me too. Though, frankly, I didn’t ever expect it to work out. I mean I got a lot of good feedback on my writing in school and things like that, but really, how many writers can actually make a living out of it?”  
“I suppose that’s true.”  
“How about you? Did you always know you wanted to do comedy?”  
“No, actually,” Conan said, pausing mid-chew. “Originally I thought I’d end up a scientist like my father. Or a historian or something.”  
“Oh really? What kind of science does he practice?”  
“Microbiology.”  
“Oof, impressive.” Gwendolyn said, raising her eyebrows before returning to her burger. “I bet he’s really proud of you.”  
Conan shrugged. “I guess so. I mean, I hope he is.” He dipped a french fry in ketchup. “I know he and my mom don’t always exactly understand the kind of humor we’re going for on the show, but they appreciate that I work hard for sure.”  
“Yeah, I can only imagine what it takes to keep a show like that going,” Gwendolyn said shaking her head. “I have petrifying stage fright so I really admire that you get up there every night in front of all of those people.”  
“You did alright when you came on?” Conan said, finishing his sandwich.  
“Oh you have no idea,” Gwendolyn said with a grin. “I turned down at least two dozen offers for tv interviews over the last year. My publisher and agent were furious. When they finally called me about your show I think they fully expected me to say no because they asked in an off-hand way and were quite startled by my eager response,” she laughed. “I’d wanted to meet you for some time and figured it would be worth it…facing my fears and all. Didn’t expect this though…” Gwendolyn nervously reached for her water and began drinking to have something to do with her hands. She feared she’d revealed too much and that she was coming off as creepy.  
“I think it’s sweet that you’ll only do my show,” Conan said, smiling. “I get the exclusive. It’s not often that happens in this business.”  
“Ha, I suppose that’s true,” Gwendolyn said as she finished her meal. They paid and left the diner, walking into the dewy summer afternoon.  
“So, did you want to go somewhere? Or we could go back to my place?” Gwendolyn suggested.  
“How about a movie?” Conan asked. “There’s a multiplex a couple of blocks away. We could see if anything good is playing.” Gwendolyn assented and followed his lead. On the way a young overexcited college student stopped Conan and asked him for a photo, and was immediately joined by his posse of friends whom Gwendolyn could scarcely tell apart. Conan patiently posed with each of them, but by the time he got to the last one, a crowd formed and it was a solid forty-five minutes of photos and autographs with fans before they could proceed on their way. Gwendolyn didn’t mind at all, it was almost like getting to be a scientist observing some kind of unique test subject in a human zoo. It baffled her, however, how he could stand all these strangers invading his personal space, making demands on his time, and still smile and joke with each one of them, making them feel as though they’d each had a special, genuine encounter.   
“I’m so, so sorry about that,” Conan said as they perused the movie times. The only thing left playing was a drama they hadn’t heard much about with a lead neither of them particularly liked.   
“Let’s get one thing settled,” Gwendolyn said, turning to him. “You don’t ever need to apologize to me for that. Never again, okay? The fact that you put up with that over and over…no, I don’t need an apology. It’s no problem for me to stand there quietly and wait. Unless it’s a medical emergency or something, seriously, don’t worry about it.”  
“Yeah, you say that now,” Conan sighed, shaking his head. “It’s only been two days.”  
Gwendolyn smirked. “I suppose that’s true. But for now, I’m not bothered.”  
Conan nodded and they decided to see the movie despite their trepidations, since they were already there. About half an hour in Gwendolyn, at least, was regretting their decision. The acting was hollow and the writing was cringeworthy. Noticing that they were in the back row and had no patrons on either side, she decided to make the best of the situation. Lifting the armrest between them, Gwendolyn inched her hand across Conan’s thigh, reaching the button of his jeans. Conan grabbed her hand and she noticed out of the corner of her eye that he turned toward her, but she resolutely faced forward, refusing to move her hand. After a moment Conan relented, taking his hand back and she proceeded to unzip his fly and delicately slid her hand into his pants, brushing his cock with the tips of her fingers at first and then gently coaxing it from the confines of his jeans. Pausing to lick her palm, Gwendolyn began stroking. She noticed Conan’s breath hitch next to her but she maintained her forward stare, determined to ignore what her own hand was doing.   
After a few moments, Conan began squirming in his seat and thrusting himself into her warm hand. Gwendolyn did a quick look around of the theatre before stealthily slinking to her knees and turning to face him. Conan placed his hands on her forearms and shook his head. Gwendolyn just stared back, rubbing the tip of his cock in achingly slow circles with the ball of her thumb. It was a full minute before Conan broke, nodding and closing his eyes as she leaned forward and took him fully into her mouth. Conan was fighting to stay quiet as Gwendolyn bobbed up and down, her tongue wrapping around the head of his cock as she sucked hard on the tip. He placed his hands on her head and she sank down, taking him deep in her throat and pressing her tongue against the underside of his now-throbbing cock. He came in shuddering waves, one hand clenched full of messy auburn hair and the other gripping the theatre seat with such intensity his knuckles whitened. Breathing hard through his nose to avoid moaning, Gwendolyn pulled off with a quiet gasp, wiping her eyes, and resumed her seat next to him as if nothing happened. Conan put his softening penis back in his pants and zipped up, mopping sweat from his brow, now completely lost as to what was going on in the movie. Not that it mattered at this point.   
After taking ten minutes to compose himself, Conan leaned over to Gwendolyn. “Want to get out of here?” She nodded and they quietly stood to leave. As they emerged blinking into the mid-afternoon sunshine, Conan rounded on her.  
“Okay, what the _fuck_ was that?” he smiled exasperated, throwing up his hands.  
Gwendolyn just shrugged and smiled coyly. “I don’t know…the movie was boring and it…seemed like the thing to do.”  
“The _thing to do_?”  
“Yeah…” Gwendolyn bit her lip. “Problem?”  
“No…I mean, I guess not, I…I’m just not used to that sort of…I’ve never…not in public…” Conan exhaled dramatically. “It was just new is all.”  
“Sorry, I didn’t mean to—“  
“No, no, don’t apologize. Just threw me off a bit. Don’t get me wrong. I liked it,” Conan made his eyebrows dance. “In case you couldn’t tell.”  
Gwendolyn giggled. “Good. Because that sort of thing gets me really…hot.” She whispered, wrapping her arms around his waist.  
“Well, well, well. Maybe we should make our way back to your place then,” he bent down to give her a quick kiss and they began walking toward her apartment. As soon as they got inside, Conan pressed her against the back of the door, lifting her hands above her head and grasping both wrists in between the long fingers of his left hand. Pausing to let their lips meet, tongues dancing and swirling in ever-quickening movements before Conan slid his hand under her shirt and tenderly fondled her breasts. Pressing a leg in between hers and grinding slightly, Gwendolyn enthusiastically rubbed herself up and down his leg, small, mewling whimpers escaping her throat. Conan’s fingers trailed downward and he pulled back from their kiss to stare her in the eye as he undid her jeans and moved his fingers between her thighs, humming in delight at the silky wetness he found. Twiddling his fingers teasingly back and forth, Gwendolyn began to writhe against her constrained wrists, undulating forward into his dexterous fingers, breath ragged as she moaned Conan’s name. He increased his speed, pressing hard on her clit, her mouth falling open as her eyes rolled back. She hanged all of her weight from her wrists, propelling all of her weight forward into the hand between her legs, her body shaking and bouncing against the wooden door.  
When finally she caught her breath and got her feet solidly underneath her, Conan released her wrists and she wrapped her arms around him, nuzzling her face into his neck. They stood there holding one another, barely inside the apartment. Eventually, Gwendolyn took Conan by the hand and led him to her bedroom. Wordlessly they took off their jeans and climbed into the bed. Nestling herself in the crook of his lithe body, she closed her eyes and began to drift, feeling Conan’s lips brush the nape of her neck before sleep took her.


	2. II

Gwendolyn woke to the sensation of her hair being brushed and was disoriented for a moment before blinking the world into clarity.  
“Hey,” Conan whispered, kneeling by the bed and smiling. He’d been running his fingers through her hair to gently wake her up. “I have to head out, have to be at the studio early in the morning.”  
“Whattimeizit?” Gwendolyn slurred groggily.  
Conan chuckled. “Almost ten. We slept all day.”  
Gwendolyn nodded and rubbed her eyes. “Okay, let me follow you so I can lock the door.” She sat up and cricked her neck, yawned, and stood up, trailing after Conan to the front door.  
“Well,” he said, turning to face her. “I’d say it’s been a pretty successful first date.”  
Gwendolyn laughed. “Oh yeah, I guess so.”  
Conan leaned in and kissed her, one hand on the small of her back while he wound the fingers of the other in her bed-mussed hair. “Damn, it’s hard to leave right now,” he whispered after pulling away.  
Gwendolyn kissed his chin. “It’s hard to let you go.”   
They held each other for a moment, swaying slightly.   
“I’ll call soon, alright?”  
Gwendolyn nodded. They separated and gave a little wave. Peering out the window she saw his bouncing orange hair head down the street to hail a cab. Smiling to herself, she sat down to do some writing before heading back to bed.  
The next morning when Gwendolyn looked at her phone she had six missed calls. Instantly she panicked. She always turned off the volume while she slept, but six missed calls in one night must mean some kind of emergency. She hit play and was immediately assaulted by the voice of her best friend Missy screaming into the receiver.  
“AHHHHHH!!! GWENDOLYN!!! YOU’RE IN THE _DAILY MAIL_!!! WHY DIDN’T YOU TELL ME YOU’RE DATING _CONAN O’BRIEN?!?! CALL ME IMMEDIATELY!!!_ ”   
_Oh no_. Gwendolyn groaned. The other messages were similar. A few from acquaintances, one from her agent, and even a teasing one from an ex. She called Missy back and explained that it was only a first date, as Missy was hurt that she’d not been told such monumental news, and ignored the rest. She supposed Conan was used to this sort of thing, he probably didn’t even notice anymore. Nervously she turned the ringer back on and went back to writing. 

At about four that Tuesday when the phone rang she walked up to it, then hesitated. _You’re just going to have to get used to it_. Breathing deeply, she picked up and cautiously said, “…hello?”  
“Hey Gwen, it’s Conan.”  
Her shoulders dropped. “Whew, boy am I glad it’s you calling.”  
“Why, you were expecting someone else?” he asked.  
“Well…” she began. “I’ve been getting quite a few calls. Turns out there are some pictures of us in one of those tabloids.”  
Conan was silent for a moment. “Oh no, I’m so sorry. I didn’t even spot any of those guys when we were out. They’re pretty tricky sometimes.”  
“Not your fault,” Gwendolyn said. “It was just surprising.”  
“Well, I’m sorry to tell you that this probably isn’t the last time this’ll happen…” Conan said. “Do you…do you think you can handle that?”  
Gwendolyn nodded, then realized that he obviously couldn’t see her. “Yeah, I mean, I know it won’t be easy all the time but…to me it’s worth it. I mean…to me you’re worth it.”  
“…thank you,” Conan almost whispered. “It means a lot to me.”  
There was a moment of awkward silence before Conan cleared his throat. “So…uh…I was calling because tonight some of the guys I know from SNL are getting together for drinks. Nothing fancy, just hanging out at a bar across the street from here, and I was wondering if you wanted to come?”  
“Yeah, I’d love to!” Gwendolyn smiled.   
“Great,” Conan said. “Can you get here around 9:30? Come in the same entrance you did when you came to do the show and give the security guard your name. Say you’re there to see me and I’ll come get you.”  
“Yeah, that sounds good, I’ll be there.”  
“Okay,” Conan said. “See you then. Bye.”  
Gwendolyn said goodbye and hung up.

She chose an emerald green dress and walked through the doors of Rockefeller Plaza at 9:25. Giving her name to the security guard, he spoke into his walkie-talkie and after a few minutes of fiddling her thumbs, Conan appeared in a lavender button up shirt, top button undone, and dark wash jeans, smiling.  
“Hi!” he said, opening his arms and enveloping her in a hug. He pressed a kiss to her cheek and lowered his hands to her waist. “How are you? You ready to go?”  
“Yeah, I’m good. How about you?”  
“Good, good,” Conan said with a nod. “Come on.”   
He led her by the hand out of the building and quickly looked both ways across the street before breaking into a jog and rushing toward a small bar. As soon as the door opened several hands bedecked with beers raised in Conan’s direction. He waved in acknowledgment before leading them to the back corner. Gwendolyn recognized some of the faces immediately but figured it was best to feign ignorance as Conan began to introduce her around.  
“Hey Bill, this is my girlfriend, Gwendolyn, Gwendolyn Greene,” Conan said, gesturing toward Bill Hader. Bill extended his hand and Gwendolyn shook it politely. Just then Conan was scooped away by some comedian or another and held up a finger to Gwendolyn to indicate that he’d be back in just a minute.   
“Wait a minute…Gwendolyn Greene…why do I know that name?” Bill asked, tilting his head and pointing at her.  
“Well, I wrote a book, maybe you’ve heard of it—“  
“Holy shit!” Bill exclaimed, eyes going wide. “ _The Dragon’s Hide Curse_ , right? That’s you! Oh man, I loved it. Seriously, I’m a huge fan. Can’t wait for the next one. I’m a huge nerd, I have all the merch at home.”  
Gwendolyn laughed. “Well, thank you, I’m glad you liked it. That’s very flattering. The second one will be out next year. Speaking of, I’m a huge fan of yours. Your Vincent Price in particular is amazing.”  
“Aw, thanks, yeah, I have a lot of fun doing him,” Bill said, taking a swig of beer.  
“But man, it’ll really kill you to play a straight guy, huh?” Gwendolyn said with a smile.  
Bill giggled and shrugged. “Yeah, I honestly don’t know what it is. Just get cast as a lot of gay dudes for whatever reason.”  
“What do you mean you don’t know?” Gwendolyn said. Bill cocked his head, looking at her curiously. “It’s those cheekbones and that killer jawline, obviously.”  
Bill broke into uncontrollable giggles again. “Stop it, you’re gonna make me blush.”  
Gwendolyn laughed. “Well, you know why women like a nice jawline don’t you?”  
“Why?”  
“Actually, on second thought I probably shouldn’t say, it’s not very appropriate,” Gwendolyn pressed her hand to her forehead.  
“Aw, c’mon, go ahead,” Bill encouraged, gently pushing her shoulder.  
“Well, they say a woman likes a nice jawline because she needs a sturdy place to sit,” Gwendolyn muttered, immediately covering her face in embarrassment.  
“Oh! First time I’ve heard that one. I’ll have to remember that,” Bill said, falling once more into giggles.   
“What’s so funny?” Conan asked, reappearing at Gwendolyn’s shoulder.  
“Nothing,” Bill and Gwendolyn responded in unison, which prompted them both to start laughing again. Conan looked back and forth between them curiously before encircling Gwendolyn’s waist and leaning down to her ear.  
“Come on, I’ll introduce you around,” She nodded and waved to Bill who lifted his beer in acknowledgment. Turning around she came face to face with John Mulaney, looking oddly formal in a blazer among his mostly t-shirt clad peers. Conan took her around the group to several other writers and comedians, many of whom she didn’t know and several of whom she wouldn’t be able to remember later, before they got a couple of drinks and settled in at a table of their own.  
“Hey, is Bill seeing anyone?” Gwendolyn asked.”  
“Oh no, tired of me already?”  
She laughed. “No, not at all. I have a friend who thinks he’s cute. And she’s really foxy, so I just thought…”.  
“Now that you mention it I don’t actually know. Hey Bill!” He called out. Bill turned around, pointing at himself. Conan nodded and Bill wove his way through the crowd to their table.  
“Hey man, what’s up?”  
“Are you seeing anyone?” Conan asked.  
“Now Conan, I know we’ve grown close over these last few years, but really…”  
“Ha-ha, Bill, no seriously,” Conan asked.  
Bill shook his head. “Nope, free and clear at the moment.”  
“Are you opposed to a set up?” Gwendolyn asked. “Because I know my friend Laura is into you and she’s absolutely gorgeous.” She brought up her phone and began flicking through it before turning the screen to face him, showing an attractive raven-haired woman.  
“Wow, you weren’t kidding,” Bill leaned in toward the screen. “What’s she like?”  
“Well, she’s a visual artist. A very passionate person, creative, and a little intense, but a lot of fun too.”  
Bill chewed on his lips for a moment. “Yeah, what the hell. Set it up. Might as well, right?”   
“Great, so you’re okay if I give her your number?” Gwendolyn asked.  
Bill shrugged. “Sure. I’ll give it a shot.” Gwendolyn smiled and put her phone away.   
They spent the rest of the evening talking and laughing, Gwendolyn getting to know Conan’s friends, and around one a.m. they emerged from the bar onto the street and hailed a cab.   
“You want to come to my place?” Conan asked as they climbed in. Gwendolyn nodded and he gave the driver his address. As they sped off he intwined their fingers and leaned in to her ear. “I hope it’s okay that I introduced you as my girlfriend tonight…I didn’t know if…I thought...”  
Gwendolyn stopped him. “Yeah, I liked it. I mean, I know we hadn’t discussed it or anything, but it was…nice.”  
Conan smiled and pressed a kiss to her temple. Soon they arrived at his building and as they walked into his apartment he immediately turned and peppered her with kisses, pulling down the sleeves of her dress and running his hands over her body.  
“Wait…Wait, there’s something I need to talk to you about,” Gwendolyn said, slightly breathless.  
Conan pulled back. “Okay…,” he looked concerned.  
Gwendolyn sat on the couch and beckoned him to join her. “So you know how I fixed up Bill with my friend Laura?”  
“Yeah…” Conan replied.  
“Well, I feel like you should know that Laura and I, well, we…we…I haven’t exactly known how to tell you this but um…” she looked at him hesitantly. “Laura and I…we used to go out.”  
Conan blinked a few times, confused. “Used to go out? With… _each other?_ ”  
“Yeah,” Gwendolyn began. “I’m not…straight. I’m pansexual.”  
Conan paused for a moment. “Okay, um…I don’t…I don’t really know what that means.”  
Gwendolyn took a deep breath. “It means I’m attracted to people regardless of gender. I’ve been with men, women, trans people…I fall for the person, I don’t care about the parts.”  
Conan nodded. “Okay, okay…” He nodded some more. “I can handle that. But I mean…you’re a one-person-at-a-time-kinda-gal right? Like, am I going to be enough for you?”  
“Oh, definitely!” Gwendolyn smiled, relieved. “I’m monogamous. I just thought it was important that you know this about me. I didn’t want to hide anything from you, or find out later that it was a problem.”  
Conan shook his head. “No, it’s not a problem. I mean, I won’t lie…it’s a little intimidating I guess, but I also saw that picture of Laura and…” he smiled. “I know it’s stereotypical, but the thought of you two together…that’s pretty damn hot,” Conan laughed.  
Gwendolyn threw back her head and laughed. “Oh, you like that, huh?,” she said once she composed herself. Scooting over to Conan’s side of the couch she threw one leg over his lap and straddled him, putting her arms around his neck and placing her lips close to his ear to whisper, “So do you want to hear about it?”  
“Y-yes,” Conan stammered, placing his hands on her hips, which gently rotated on top of him.  
Gwendolyn hummed, speaking in a low, throaty whisper just inches away from Conan’s ear. “Well, it was sophomore year of college, and Laura lived across the hall from me. I noticed her right away. Her full lips,” she ran her fingertips across Conan’s mouth. “Her luxurious black hair,” she trailed her hands over his scalp. “Her beautiful, pale breasts,” she caressed his chest. Conan swallowed hard and could feel his cock stiffening against the confines of his jeans as Gwendolyn continued to move against him.  
“One night she came to my door because she needed quarters for laundry. When I turned around to get them, she followed me into the room and closed the door behind her. I didn’t know it, but she’d been watching me all semester, too. She backed me up against the bed and took off my shirt, never saying a word,” she lifted off Conan’s shirt. “And she began to massage my breasts,” she ran her fingers over his chest. “Before sliding her hand down and taking off my pants,” standing up, she undid Conan’s jeans and pulled them down, his erection evident underneath his boxers. “First, she slowly rubbed me through my underwear,” she cupped his hard cock, stroking it through the material of his boxers, the pre-cum moistening the fabric. “Then she peeled them away and put her fingers inside me,” she had him lift up so she could slide down his boxers, pulling on his cock with increasingly quick movements. “Then, when I was practically begging for it, she knelt between my knees and began licking me,” Gwendolyn leaned down and took Conan’s pulsing cock in her mouth. He let out an unholy groan, thrusting deep into her throat. Pulling off for a moment, she stroked with incredible speed. “And I ground myself into her face, and I came so hard, _so hard_ ,” then she resumed sucking and swirling her hand, using her left hand to cradle and fondle his balls and with three more thrusts Conan expelled his cum with a prolonged moan, rocking his hips back and forth, head thrown back in rapture.  
After swallowing and slowly rising to her feet, Gwendolyn sat next to him on the couch. It was a few moments before Conan could open his eyes, and when he did he didn’t immediately speak. Gwendolyn leaned in next to him, placing her head gently on his shoulder.   
“Damn…that was…” he finished with a whistle.  
Gwendolyn chuckled. “Glad you enjoyed it.”  
He reached across and patted her face. “I’ll say.”  
They sat there quietly for a few moments, Conan leaning over and kissing her, removing her shirt and bra, running his hands over her pale skin, making small patterns in her flesh as he worked his way down. Pulling off the underwear and tossing them aside, he began using his fingers to stroke between her legs, kissing and lightly nipping her neck before working his way down. Sliding his tongue in a circle around her clit he heard her breath hitch, and focused his actions tighter and tighter until he was sucking full force on her clitoris, making her writhe uncontrollably underneath him, gasping and panting, her hands gripped in his orange hair and her hips bucking into him as she dripped down his face. Thrusting two fingers inside of her and crooking them toward his nose, he pushed her over the edge, and the trembling that began around his fingertips erupted outward, splaying her against the couch as she called out his name between moans and screams.  
Conan cradled Gwendolyn in his arms as she came down from her orgasm, allowing her naked flesh to tremble softly against him until she came back to equilibrium. “Want to go to bed?” he asked after he felt her breathing return to normal. He felt her nod against his chest and she stirred, standing up and rooting around for her clothes. She grabbed her t-shirt and underwear and left the rest. Climbing in bed together Conan wrapped himself around her, tucking her into the curve of his body. He had to admit it wasn’t the most comfortable sleeping position, but he didn’t care, he wanted the most points of contact he could get. Turning to double-check that the alarm was set before re-nestling, Conan flipped off the light, whispering a soft, “Goodnight,” into her mass of auburn hair before sliding off to sleep.  
Jarring, the alarm shot Conan out of bed the next morning and he reached over to slap it off, throwing his legs over the side of the bed and rubbing his face. It was a full minute before he remembered he was not alone. He turned around and Gwendolyn sat up stretching her arms above her head and turning to look at him sleepily.   
“Good morning,” she smiled crookedly.  
Conan smiled and leaned across the bed to give her a quick kiss before standing up and heading to the bathroom. He started the shower, undressed, and jumped in. He was beginning to apply shampoo when he heard, “Want some company?” from outside of the shower curtain.   
Peering outside and wiping his face, he saw Gwendolyn standing naked in the doorway of the bathroom. “Oh ho ho, I can tell you’re going to make me late,” Conan chuckled.  
Gwendolyn just raised an eyebrow.  
“Ugh, fine. Get that ass in here,” he said, pulling back the curtain. Gwendolyn climbed in and pulled the curtain shut behind her. “Just let me finish washing up and then you can get in here.” Conan said, scrubbing himself quickly while Gwendolyn stood at the back of the shower, arms wrapped around herself. “Okay, your turn.” They switched spots and Gwendolyn washed her hair while Conan (generously) washed her breasts. After she finished scrubbing herself down she noticed that Conan was hard.  
“You know, shower sex sounds fun in theory, but why do I think it would end in a phone call to 911?” Gwendolyn said, wiping water away from her face.  
Conan nodded. “Yeah, my center of gravity is in my neck, so frankly, I don’t think it’s the best idea.”  
Gwendolyn concurred, so they got out carefully and dried themselves before making their way to the bed. “Okay, um…I need to be at the studio in half an hour…” Conan said, looking at the clock, then looking at Gwendolyn standing naked before him.  
She grabbed the hair at the back of his head. “Well, you better hurry up and _fuck me then_.”  
Conan kissed her violently, throwing her against the bed and laying on top of her. He thrust his fingers between her thighs, working hard and fast to arouse her for a few minutes before reaching in his bedside drawer and fishing out a condom. Tearing it open with his teeth, he applied it hurriedly and thrust into her, taking her right leg and tossing it over his shoulder, ramming deeper inside of her than he had before. Using his left hand he reached between them and fiddled her clit in time with his movements, pounding into her with such ferocity that one of the photos on his wall was knocked loose. Gwendolyn was yelling, “ _Fuck, FUCK, Conan_!” and he could tell she was getting close. He sped up, angling her hips so he could penetrate her even deeper. Gwendolyn began to tighten and twitch around him and he felt himself lose control, gasping her name as the tightness of his orgasm burst forth from inside, and they fell together in helpless waves of elation.  
Putting her leg down and panting into the sheets, Conan rolled off of her. “Well, off to work I guess…”  
Gwendolyn burst out laughing. Conan joined her, and once it dissipated they finally stood up and got dressed, leaving the apartment with a couple of minutes to spare.

Conan called her on Friday after he wrapped filming for the week and Gwendolyn told him to head over. When he got there she was on the phone and held up a finger to indicate she’d be just a minute and gestured that he could sit on the couch while she disappeared into her bedroom. Conan, however, could overhear the conversation.  
“Oh yeah? So he had a nice dick? Uh huh…yeah…Did he go down on you though? Yeah…yeah Conan too…Yeah…Did you cum though? That’s good. Did he like that? Uh huh…yeah. So you’re getting together again, right? Nice. Yeah…Yeah, he’s pretty sexy. Yeah, nice…I gotta go though, Conan just got here. Ha, yeah, that’s for sure! Okay, talk to you later, bye.”  
Gwendolyn walked into the living room and placed her hands on Conan’s shoulders, rubbing gently and kissing him on the cheek. “Hey, how was your day?”  
“Oh pretty good…who was that on the phone?” Conan asked, trying to sound casual.  
“Just Laura, she was telling me about her date with Bill,” Gwendolyn said, walking around the couch and draping her legs across Conan’s lap. He absentmindedly began running his fingers up and down her shins.  
“I couldn’t help but overhear…do you talk like that all the time?”  
“What do you mean?” She asked  
“All those…details,” Conan asked nervously.  
“Well…yeah. I think all women talk like that. Or at least most do,” Gwendolyn shrugged.  
“So you’re saying…all those things you just learned about Bill…which are, frankly, a little horrifying that you know, Laura also knows about me?”  
Gwendolyn pulled a face. “Is that bad? I’m sorry. It’s just natural. We’re good friends. I think all women share that sort of stuff with their friends.”  
“Yeah, but…” Conan shook his head. “That’s really personal, I mean, wouldn’t it bother you if I told the guys all the details about our sex life?”  
“Well…no, not if the sharing was equal and if it made you feel closer to one another. Honestly, it’s lovely and it really cements a friendship. Have you ever tried it?”  
Conan laughed. “No, well I mean there’s “locker room talk” but that’s not the same thing…”  
“Why don’t you try it? You and Bill are friends, right? Why don’t you talk about me and Laura?” Gwendolyn suggested.  
Conan shook his head. “I wouldn’t even know how to start…”  
“Just give it a shot next time you’re together and see how it goes,” Gwendolyn said. “Honestly, it can be really helpful, too. I’ve learned a lot of great sex tips from friends over the years. Not that you need any,” she winked.  
Conan considered that for a moment. “We’ll see, I guess. Anyway, how was your day?”  
“Oh, just some writing and editing, nothing special. I did make lasagna though if you’re hungry. It should be just about finished.”  
“Yum,” Conan exclaimed. Gwendolyn got down some dishes and set the table and they sat down to eat. Conan had seconds, leaning back afterward to rub his belly in gratitude.  
“I’m glad you liked it,” Gwendolyn said as she gathered up the dishes.  
“Let me do that,” Conan insisted.  
“How about you wash and I’ll dry?” Gwendolyn suggested.  
“Deal.”  
They sank into a calm rhythm of wash, rinse, dry; silent and comfortable with one another as the night ticked by outside of the peaceful apartment. The next couple of months went on much the same, spending the weekends together when Conan wasn’t filming as long as neither of them had another event, and getting together as often as they could on the weeknights, even if it was only for a few hours. 

  
Conan walked into the pleasantly quiet sushi restaurant and scanned the room, eyes catching Bill seated at a table in the back left corner. Raising a hand in acknowledgment and getting a small wave in return, he strode toward him, clapping him warmly on the shoulder.  
“Hey man, good to see you!” Conan said, sitting down.  
“You too, man. Been a while,” Bill took a sip of water. “How’ve you been?”  
“Oh, you know, pretty good I guess. Can’t complain, really.”  
A waitress appeared at Conan’s shoulder, asking if they needed a moment to look over the menu. This being one of their favorite places, however, they both rattled off a couple of their usual rolls of choice and handed her their menus with their thanks and she walked back to the kitchen.  
“So work’s going well?” Bill asked.  
Conan shrugged. “Yeah, I suppose. It can be a grind sometimes, you know, but ultimately I enjoy it. How about you? How’s the show going?”  
“Well, it’s gotten better,” Bill said. “I still get anxious, but not as bad as in the beginning.”  
“That’s good to hear,” Conan took a sip of water.  
Bill nodded. “So how are things going with Gwen?”  
Conan smiled. “Honestly, great, I mean she’s smart, funny, sexy…I got really lucky.”  
“That’s awesome, man. Good for you.”  
“How about you?” Conan asked. “How are things with Laura? You two have been together a little while now.”  
Bill nodded. “Yeah, yeah, things are going well. She’s kind of…mysterious I guess? I don’t know, just hard to read sometimes. But exciting. Like, I’ve never been with a woman who’s so…” Bill leaned in and lowered his voice a little. “…wild.”  
Conan chuckled appreciatively. “Oh yeah?”  
“Yeah, I mean..” Bill lowered his voice further. “I really hope she told you and I’m not putting my foot in my mouth by saying this but, um, you know that Gwen and Laura used to, uh, go out…”  
Conan nodded, raising his eyebrows. “Yeah, she told me and…yowza.”  
“Right?” Bill said through the side of his mouth, tilting his head forward. “Laura told me some things and…goddamn.”  
“Gwen too…whew,” Conan comically pulled at the collar of his shirt.   
Bill broke into his signature giggles. “You don’t think they’d mind us talking about this, do you?”  
Conan shook his head. “I don’t think they can. Have you heard some of the things they say about us? It’s crazy!”  
“Oh my goodness,” Bill sat back, rolling his eyes. “The other day I walked into the room and she was on the phone describing the dimensions of my dick to Gwen over the phone. And when I confronted her and said ‘What the hell?’ Her response was, ‘I could tell you about Conan’s if that makes you feel better.’ _No! Argh!_ ”  
Conan threw back his head and laughed, hands on his chest. “I know, I know, it’s insane. I overhear their conversations sometimes and they go into such detail,” He shook his head. “But I asked Gwen about it and she said she really likes sharing and that us guys are missing out by not doing it.”  
“Huh, I guess I never thought about it like that,” Bill said, half to himself.  
“Yeah…” Conan said, rubbing the condensation on his water glass. “So…want to give it a try?”  
Bill gave a contemplative shrug. “Sure, I suppose. Why not?”  
“Okay, so…” Conan began, looking around the restaurant cautiously before leaning forward and lowering his voice. “So you said Laura was ‘wild,’ how do you mean?”  
Bill leaned forward too and suddenly they were like two teenage boys sharing a dirty magazine. “Well,” he started, eyes darting back and forth. “For instance the other night she asked me to, uh, tie her up…”  
“Oh yeah?” Conan smirked.  
“Yeah,” Bill nodded eagerly. “I’d never done anything like that before. And it was pretty hot, only…” he lowered his voice further and began talking half through his teeth. “She wanted me to slap her.”  
“In the _face_?” Conan grimaced.  
Bill nodded, looking a bit queasy. “I told her, I said, ‘I’ll spank you all day, no problem, but I just can’t do it, I can’t hit a woman in the face,” he shook his head. “No matter how badly she says she wants it there’s just this deeply engrained part of me,” he gestured to his chest. “That just can’t, you know?”  
“Yeah, I think I’d have a hard time with that one,” Conan nodded.  
“Yeah…I mean it was fun, we had a good night and I think she enjoyed herself still, but I also felt like she was a little let down,” he took a drink of his water. “How about you though? Laura actually made a comment back when we first started dating that, uh, Gwen must be over there giving Conan ‘quite the education’,” Bill giggled.  
“Well, she’s not wrong, I suppose,” Conan laughed. “She can be very…adventurous, um, for instance the first week we were dating we went to go see a movie that happened to be terrible, so in the middle of it she, uh, started going down on me in the theatre.”  
“Nice,” Bill said, nodding. “Can I ask, does she enjoy doing that? Going down?”  
“You know, it’s weird,” Conan leaned in and lowered his voice even more. “She _loves_ it. I mean, I’m waking up practically every other day with my dick in her mouth. Honestly, sometimes I’m not even in the mood until she’s partway through, but she is persistent.”  
“Goddamn man, you are lucky,” Bill said, shaking his head. “Don’t get me wrong, I’m not complaining. Laura and I have sex all the time and it’s great, but she apparently has a very strong gag reflex so that’s not something she likes to do.”  
Bill saw the waitress approaching with their food so he straightened up and they accepted their plates, thanking her and making sure she was out of earshot before resuming their conversation.  
“Yeah, that’s too bad,” Conan shook his head.   
Bill nodded, popping a slice of Dragon Roll into his mouth. “Yeah, but, she finds…other ways…to make up the difference.”  
Conan looked at him questioningly. “How do you mean?”  
“Well,” Bill gestured vaguely in the air with his chopsticks. “The other night she let me, you know, use the back door.”  
“Really?” Conan asked. “Gwen, I know, is not really into that,” he said, waving his hands. “I mean, maybe it’ll come up for an anniversary or something, but I’m not holding my breath.”  
Bill chuckled. “Yeah, I was pretty surprised,” he said. “I hadn’t done it before, but she said she had a handful of times. But unfortunately I think she was doing it for my sake because she didn’t really seem into it, more like a “grit-your-teeth-and-bear-it” kind of thing,” he said, pausing to chew. “Which isn’t what I want. I mean, I had a good time and all, yeah, but it’s not something I’m in a rush to do again unless it’s with someone who really wants to be a part of it.”  
Conan nodded. “That makes sense.”  
“Let me ask you,” Bill said, swallowing. “How do you feel about going down yourself? I know a lot of guys don’t like doing it.”  
Conan shook his head. “Personally I think that’s ridiculous,” he swallowed a bite of tuna hand roll. “First of all, I don’t understand those guys who expect a woman to go down and aren’t going to do anything in return. Selfish. But beyond that, I just really enjoy doing it. There’s something about her being so…vulnerable and open like that. Plus, it just feels good to make her feel good.”  
Bill nodded. “I agree. Though have you ever dated a woman who won’t let you do it?”  
“Ugh, yes,” Conan replied around a mouthful before taking a moment to swallow. “The worst. I don’t know what you do with that.”  
Bill shook his head. “Me neither. Never works out.”  
They ate in silence for a while, working their way through their meals before Bill piped up. “So, you and Gwen, you think you’re in it for, you know, the long haul?”  
Conan considered for a moment. “Well, I’ll say this: I am. I know it’s still pretty early days but as of now I’m all in. We haven’t really discussed anything long term, you know, so I don’t know if she feels the same way, but I hope so.”  
“Any reason you haven’t brought it up?” Bill asked, picking around the remnants of his plate.  
Conan tipped his head back and forth. “Haven’t wanted to scare her off, I guess? I don’t know, I just feel so lucky to be with her that sometimes I…” he paused, looking down. “Sometimes I get so scared that I’m going to mess it up.”  
Bill shook his head. “No, man. I mean, I get it and I think that’s natural and all, but anyone who sees the two of you together can tell she’s crazy about you.”  
Conan idly tapped his chopsticks on the side of his plate. “I guess it’s just hard to believe. How about you? Do you see you and Laura going the distance?”  
Bill held out his hand and made a teetering motion. “You know, like I said, she’s very…mysterious. Like she’s incredibly passionate, always up for sex and hanging out, but if I try to get romantic, she gets uncomfortable and instantly tries to flip it back to sex. So I can’t say I really know her better now than I did a couple of months ago.”  
“Huh, and you’re okay with that?” Conan asked.  
Bill shrugged. “I don’t know. At this age I feel a bit…silly doing the whole casual sex thing, but at the same time I can’t pretend I’m not having fun, so for now I’m just rolling with it and waiting to see if it turns into anything.”  
“Fair enough,” Conan nodded. The waitress came by with the check, they paid, and stood to leave.  
“Well, this was really good, man. I’m glad we were able to catch up,” Bill said.  
Conan nodded. ”Me too. We’ll have to get together again soon.” They walked out of the restaurant, going in for a quick hug before separating and heading to their cars. As he turned the ignition, Conan had to admit that Gwendolyn was right, it felt good to share with Bill


	3. III

**Notes for the Chapter:**

> Okay, Okay, so I realize Benedict Cumberbatch being on Conan’s show during this time period does not make sense. But, I figure this is my story, and as a silly person writing lurid fan fiction about the glorious Conan O’Brien, does reality really seem like my biggest concern? I also know Andy wasn’t on the show during this time, but I love him so he’s sticking around. Just go with it.

Gwendolyn walked into Conan’s office, smiling broadly and carrying a basket under one arm. “Hey hun, I brought lunch,” she said, walking across the room and behind the desk to give him a quick kiss before planting the basket on the desk and beginning to unload it.  
Immediately the round-cheeked face of Andy Richter popped up in the doorway. “Did I hear something about lunch?” he asked, tapping his fingers together in anticipation.   
Gwendolyn laughed but Conan let out a long, exasperated sigh. “You are like a homeless, mongrel dog. Seriously, the mere mention of free food and you just _materialize_ like some kind of mooching specter!”  
Andy held out his hands in mock appeasement. “What can I say? She’s a good cook.”   
Gwendolyn rooted around in the basket, pulling out one Tupperware container and placing it before Conan, taking out a second and setting it before herself, then peering deep into the basket, feigning concern that it was empty for a moment before withdrawing with exaggerated surprise a third container for Andy. “Ahhh, thank you. What’s on the menu today?” Andy asked, pulling up a corner and giving it a sniff.  
“Well, I don’t know if you two will like it, but it’s a twist on a Liberian dish. Peanut Butter Bell Pepper Ribs. I know it sounds weird, but just give it a try. I toned down the heat for your sake,” she rubbed Conan’s shoulder. “So hopefully it’s okay.”  
They all crowded around the desk and Gwendolyn reached into the basket to pass around forks and napkins. “Alright…” Andy said after the first few bites, chewing thoughtfully. “This is weird but…amazing. Somehow the peanut butter and the beef and the heat…works? I really never would’ve guessed.”  
Conan nodded. “I don’t know what’s in it, and frankly, I don’t care. It’s really good.”  
“Not too spicy?” Gwendolyn asked.  
Conan shook his head. “Just right.”   
They finished the meal in silence and Gwendolyn packed up the basket again. “You know, I don’t think I’ve had African food before,” Andy said.   
“Oh, I’ll have to make Sambusas then,” Gwendolyn said. “They’re Somalian meat pockets, and they’re delicious.”  
Andy clapped a little and she smiled. He thanked her for the meal and headed back to his office.  
“You have a busy day today?” Gwendolyn asked as she gathered up her things.  
“Oh, just a typical day for the most part. We have a lot of crazed fans trying to get into the studio though because we have Benedict Cumberbatch on toni—“  
“ _WHAT_?!” Gwendolyn shrieked at such a high pitch and rounded on him with a ferocity that set his heart thumping.  
“Jesus Christ, what was that?!” He asked, hand to his chest, eyes wide.  
“Sorry, I, um,” she stammered, trembling hand at her temple. “I’m a bit of a fan…”she said sheepishly.  
“Oh really?” Conan narrowed his eyes. “How did I not know this?” He thought back, tapping his chin. “You know what, now that you mention it, if I look back at the nights when we watched his films you were particularly…affectionate after, weren’t you?”  
Gwendolyn was turning a deep shade of pink. “I-I suppose that’s true…” she muttered, not making eye contact.  
Conan stood up, rounding on her. “Mmhmm, I see how it is, Greene. Get your fancy British boy to turn up the heat and then you have the old Ginger Quipster put out the fire, eh?”  
That one made her smile. “Guilty,” she said, still unable to look up at him.  
“So,” he said, playfully pushing her hair back from her ear. “I suppose you want to stick around and watch the show. Maybe…meet Mr. Cumberbatch?”  
Gwendolyn self-consciously rubbed her arm. “Yes, please,” she answered in a small voice.  
Conan laughed, sliding his arms around her waist and pulling her into him, sighing. “Fine, I suppose you can stay,” he said, gently swaying them back and forth. “But only because I happen to know he’s happily married.”  
Gwendolyn chuckled into his chest. “Thank you.”  
She spent the next few hours in Conan’s office, doing her best to stay out of the way, exploring all of the fan art and little knickknacks that decorated his walls and desk. After a while, Conan burst in wearing his suit and tie, makeup freshly done and hair coiffed. “Come on, he’s here. I’ll take you backstage and you can meet him.”  
Gwendolyn nodded, wiping her now-sweating hands on her dress and instantly regretting that she hadn’t taken a second glance in the mirror. She followed Conan, practically jogging to keep up with his long strides, stopping short outside of a door marked ‘Benedict Cumberbatch’ which Conan knocked on lightly.  
“Come in,” came a familiar British voice.  
Conan opened the door with a wave. “Hello Benedict, nice to meet you, I’m Conan,” he said, extending his hand.  
Benedict stood up, shaking his hand. “Hi Conan, nice to meet you, too.” His eyes darted quickly to Gwendolyn lurking quietly behind Conan.  
“This is my girlfriend, Gwendolyn Greene,” Conan said, stepping aside and gesturing behind him. “She’s a big fan of your work.”  
Benedict extended his hand to her and she shook it. “Thank you, very nice to meet you,” he said, and then a confused look crossed his face. “Wait a minute,” he said, holding up a hand and snapping. “Gwendolyn Greene, the author?”  
It was as if her brain was on delay. She had to remind herself that that was, indeed, her name and profession. “Y-yes, that’s right,” she said, clearing her throat.  
“Oh, Sophie and I loved your book, we can’t wait for the next one. It comes out soon, right?”  
Gwendolyn nodded, struggling to form sentences. _Aren’t you supposed to write for a living?_ “Yes, next week.”  
“Brilliant, I’ll be first in line to buy it,” he smiled.  
“That’s very kind,” Gwendolyn said, a thought occurring to her. “Actually, hold on, I’ll be right back, wait just one minute—“ and she dashed out of the room, leaving the two of them looking confused. Running full speed back to Conan’s office and back, she took a half a moment to catch her breath before re-entering the room.  
“Here,” she said, handing Benedict a book. “Advanced copy. Enjoy.”  
“Oh wow,” he said, turning it over. “Thank you, this’ll be a real treat for the flight home. Will you sign it for me?”  
Gwendolyn nodded and he handed her back the book. It took all of her concentration to keep her hand from shaking as she wrote a little message and signed her name.  
“Thank you,” he said as she gave it back to him.  
“You’re welcome.”  
“Well, we should probably go. It’s about time for us to get started,” Conan said, placing his hand on her shoulder. Gwendolyn would’ve been embarrassed to admit that she forgot he was standing right behind her the entire time. She nodded and waved goodbye to Benedict, following Conan out of the room and back down the hall toward his office where she gathered up her things.  
“Thank you for that,” she leaned in to give him a kiss.  
Conan smiled. “Sure, no problem,” he shook his head and chuckled. “I can’t believe you gave him my copy of the book!”  
“I know!” She said. “Thank goodness I hadn’t written anything to you in it already. Imagine how embarrassing that would’ve been.”   
Conan laughed, pressing his forehead to hers. “Did you want to stay and watch the show?”  
“Yeah,” Gwendolyn said. “I’d love to.”   
“Okay, come on. I’m sure we can find you a seat. Just leave your stuff here.”  
Gwendolyn sat down and got comfortable as they started the show, clapping and laughing through the monologue and skits, Conan giving her a wink here and there during commercial breaks.   
“Alright, everybody, I’d like to welcome my next guest, star of BBC’s ‘Sherlock,’ ‘Star Trek:Into Darkness’, and the upcoming ‘Patrick Melrose,’ Mr. Benedict Cumberbatch!” The audience went wild, screaming as Benedict emerged and shook hands with Andy and Conan, taking his seat and straightening his suit.  
“Good to see you, Benedict.”  
“You, too, Conan. Good to be here.”  
“Now,” Conan began, gesturing to the crowd. “You get quite the reaction when you come out here.”  
“Yeah…” Benedict said sheepishly.  
“Now I have to talk to you about that. Before the show I was talking to my girlfriend, Ms. Gwendolyn Greene, who’s in the audience tonight. Jeff, let’s get a camera on her and embarrass her for a second.”  
Gwendolyn laughed and covered her face. “Yeah, there she is, trying to pretend she doesn’t know me, as per usual,” Conan chuckled. “Very good, so, I have a bone to pick with you,” Conan continued, gesturing to Benedict. “I was talking to her and I mentioned casually ‘Oh yeah, we have Benedict Cumberbatch on the show tonight’ and she _screamed_ at such a high pitch I swear to God my eardrums exploded, it was crazy.” The audience laughed. “Now I’ve certainly never made her scream that loud…” More laughter. “But somehow you managed to and you weren’t even in the room.” Conan chuckled. “So what I want to know is, what is it like, getting this kind of reaction from people?”  
Benedict laughed and rubbed his face. “Honestly, it’s all a bit embarrassing. I mean I look in the mirror and I certainly don’t get it, so to go outside and get that sort of reaction is more than a bit unnerving.”  
They continued the interview, discussing Benedict’s upcoming project and when the show wrapped Conan came down and gave Gwendolyn a hug and a kiss on the cheek, which prompted an “Awww!” from some of the audience members that were still filing out. Gwendolyn blushed and followed him backstage, picking up her stuff from his office while he went to the restroom to wash off his makeup and change into his casual clothes.   
They left the building and caught a cab, deciding to spend the night at his place. He opened the door to the building and they began to ascend the stairs.   
“Can I ask, why do you always make jokes saying you’re bad in bed? You know it’s not true,” Gwendolyn asked.   
“Yeah, well,” Conan said, taking another step. “It’s funnier that way. There’s no comedy in saying, ‘Oh my girlfriend and I have a great sex life and I love her’.”   
Conan froze, one foot hovering above the next step. It would’ve been amusing if it wasn’t so serious. He looked back at Gwendolyn and she’d stopped about three steps behind him, her mouth hanging open. “You said…love…” she murmured.  
Turning on the step, swallowing with a suddenly dry mouth. “I did.”  
“Did you mean it?” she asked.  
He paused for a moment, looking back and forth between her luminous green eyes. “I do.”  
She nodded, taking a deep breath. “I love you, too.”  
“You do?”   
“Yeah,” They both smiled. She climbed up to meet him, kissing passionately as they held on to the banister for balance.   
“Let’s get inside,” Conan whispered as they separated. She nodded and followed him the rest of the way up.   
The door closed behind them and they began to undress, eyes blazing as they stared at one another, Gwendolyn walking backward toward the bedroom as she tossed articles of clothing recklessly about every few steps. Conan pursued her hungrily, climbing in the bed after her naked form, sliding his hands up her body and into her hair. She wrapped herself around him, descending into their kiss as they threatened to consume one another. Conan rubbed his hardening cock between her legs without entering her, stroking himself against her clitoris. She ground herself against him, small moans reverberating from her throat as she ached for friction. He broke their kiss and lowered himself between her thighs, diving in and twisting his tongue around her clit before sliding his fingers inside of her and applying gentle, pulsing pressure. Once she was pressing herself hard into his face, Conan stopped, pulling his hand free, and Gwendolyn let out a desperate whine of dissent.   
But then Conan laid on his back and turned his head toward her before patting her thigh. “Get on top.”  
“Yeah?”   
“Yeah, come on,” he said, nodding.  
“Okay, just pinch me if it gets to be too much, okay?”  
Conan nodded and she climbed on top, straddling his face with her thighs and slowly lowering herself toward his eager mouth. As he began licking and sucking on her, she held on to the top of the headboard, gently grinding herself down into his tongue, loving that she could control the pressure. Increasing his speed, Conan put his fingers back inside of her and she bounced and ground more fervently against him, panting hard as she dripped down his cheeks. Starting to shake, almost the entirety of her weight was balanced against his face and still he wasn’t indicating that he’d had enough. Screams emanated from her as she came, rocking violently back and forth, trembling and thrashing above him as she called out his name.  
Climbing off of him and flopping onto the bed, Conan gasped and wiped his face, breath staggered, his hard cock leaking against his stomach. Taking a couple of minutes to catch their breath before turning to one another, mouths seeking hungrily, tongues dancing together. Conan positioned himself between her legs and slid his cock inside of her, groaning at the familiar moist pressure that enveloped him. Achieving a steady, swirling rhythm, Conan found himself gripping her more tightly than he had before, desperately folding her into himself with each rotation, pressing his lips to every bare inch of flesh he could reach.   
As he felt the threat of his orgasm approach, he pressed his lips to her ear and whispered, “ _I love you. I love you.”_  
Breathily she responded. _“I love you, Conan. I love you so much_.” Soon after they both became incapable of articulating words as their bodies thundered together, trembling and receding as they gasped for air and for each other.  
They rolled apart, sticky and sweaty, Conan’s orange hair plastered against his forehead as he reached over to brush an errant strand away from Gwendolyn’s face. She smiled at him coyly and he rolled over to place a gentle kiss on her cheek before rolling back, sitting up, and grabbing a t-shirt and boxers to get to sleep. Gwendolyn found a shirt and underwear of her own and they snuggled up together, turning off the light.  
“I’ve wanted to say that for a long time,” she whispered into the darkness.  
“Me too,” Conan replied.  
“Why didn’t you?” she asked.  
“I don’t know…I was just scared, I guess,” he replied softly.  
“Scared of what?”  
“Of scaring you away,” Conan said. “Of losing you.”  
She turned over in bed to face him. He could barely see her outline in the dim moonlight seeping through the room, but he sensed her eyes on him.  
“As long as it’s up to me,” she whispered. “I’m not going anywhere.”  
“Yeah?” He breathed.  
“Yeah,” she responded, nestling herself into him and kissing the hollow of his throat. He pressed his lips to the top of her head and wound his arms around her, pulling him to her tightly. They breathed one another for a few minutes before unraveling and sliding into a contented sleep, both warmed by the other’s presence.

A couple of weeks later Gwendolyn was on the couch flipping through her phone while Conan sat across from her reading a book on the Civil War in the few extra minutes he had in the morning before heading to the studio.  
“Oh no!” She exclaimed, sitting up.  
“What?” Conan asked, peering at her over the top of his glasses.  
“Laura broke up with Bill!” Gwendolyn frowned.  
“What?” Conan said. “Really? I thought things were going okay. What happened?”  
Gwendolyn rolled her eyes. “Ugh, she’s going back to her ex,” she made a face. “He’s a real sleaze-bag. They’ve been on and off for years and I always try to tell her what garbage he is but she won’t hear it,” she shook her head. “Aw, poor Bill,” she frowned. “I should make him some cookies or something. Do you think he’s busy?”  
Conan shrugged. “I don’t know if he’s free, but you could certainly leave them at his door or something.”  
“You have his address?”  
“Sure,” Conan said, fishing his phone out of his pocket. “I’ll give you his number too and you can text him if you want.”  
“Oh, I feel so bad. It was my idea to fix them up,” Gwendolyn pressed a hand to her chest.  
Conan shook his head. “Not your fault. It lasted a while, and you couldn’t have known for sure whether or not it would work out,” he said, closing his book and standing up to find his shoes and head out the door. “Plus, I think it’s nice that you want to make him cookies.” He leaned down to kiss her goodbye.  
“Oh, you know me, I try to fix everything with food,” she smiled, kissing him back.  
“Maybe save me a few if you make extra?”  
She nodded, telling him to have a nice day and saying goodbye. Once he was out of the door she set to baking. She texted Bill to see if he was home and he said yes, but when he asked why she wanted to know she just said she was going to head over soon to drop something off and didn’t go into detail. Not knowing Bill all that well she figured the classic chocolate chip were a safe bet, and they were easy enough to whip together. After they’d baked and cooled she found a decorative basket in her closet and decided she would stop at the liquor store on the way to his place. After all, she didn’t even know if he liked sweets, and if nothing else the wine would help him get over a break-up. She bundled up warm when she saw that it was, once again, snowing outside, and left the apartment, heading downstairs and around the corner to the liquor store. Buying three bottles of a nice Pinot Grigio and placing them in the basket among the cookies, she hopped in a cab and gave the driver Bill’s address.   
When she reached his building he buzzed her in and she climbed the stairs, knocking gently and waiting a couple of moments.   
Bill opened the door, Gwendolyn held out the basket, and he broke into giggles. “Awww, cookies and alcohol! Just what I wanted!” She laughed. “Come in, come in.”   
Gwendolyn sat the basket down on the counter and Bill took her coat. “This is really nice of you,” he said when he came back into the kitchen.  
“Ah, well, you know…I felt kind of bad,” she said, looking down and fidgeting a bit.  
Bill shook his head. “No, don’t. It’s okay. I mean, yeah, I’m bummed, but I think ultimately it’s for the best,” he peered into the basket. “Now what do we have here?”  
“Chocolate chip and Pinot Grigio. Is that a good pairing?” She chuckled. “I don’t know, but I figured if you didn’t like cookies there was a good chance you’d like the wine.”  
“Oh, I have a terrible sweet tooth,” Bill said, selecting a cookie and chomping into it. He hummed appreciatively. “Really good, thank you,” he said over a mouthful. “Now I can be single, fat, and drunk!” Gwendolyn laughed, taking a seat at the kitchen island.  
“Will you join me in a glass?” Bill asked, reaching in a drawer to grab a corkscrew.  
“I don’t know…” Gwendolyn said, looking at the clock. “It’s pretty early…”  
“Yeah,” Bill shrugged. “But it’s my only day off this week. Come on, what else do you have going on today?”  
Gwendolyn tipped her head back and forth. “Ah, okay, you twisted my arm. Pour me one.” Bill got down two glasses and filled them, handing her one. She began sipping it delicately, but Bill took half of his glass down in one pull. Gwendolyn sped up a bit so as not to make him self-conscious.  
“So you’re doing okay though?” She asked, hoping she wasn’t prying.  
“Well,” Bill gestured to the living room, motioning for her to follow him and grabbing the bottle of wine. She couldn’t help but notice he topped off his own glass and did the same to hers as they sat down on the couch. “I guess I’d be lying if I said I didn’t like her quite a bit. But there was a part of me that always knew things were a little…unbalanced.” He said, taking another big gulp of wine.  
“How do you mean?” Gwendolyn asked. She finished her glass and Bill immediately poured her another without asking.  
“Well, if I ever tried to get serious, you know, talk about the future, anything like that, she’d change the subject pretty quickly. She didn’t seem interested in much besides…you know…sex,” Bill said, draining his glass. He tipped the last of the bottle into his glass and stepped quickly to the kitchen to open the second one, filling it the rest of the way.  
Gwendolyn nodded. “Yeah, that sounds familiar.”  
“Oh, right!” Bill exclaimed, pointing at her. “You two used to go out, so I guess you’re the right person to be talking to. How did it end with you?”  
Gwendolyn shook her head. “Well, I was young and naïve and she broke my little college girl heart,” she said, draining her glass again only to have it refilled immediately. She was starting to feel a gentle buzz. “It was a long time before we were able to be friends after.”  
Bill nodded. “You were pretty serious then?”  
“Well, I thought we were,” Gwendolyn shrugged. “But I’d only been with one woman before her and I just wasn’t used to her…intensity I guess. It made some things seem realer than they were.”  
“ _Right_?” Bill said, throwing back another glass and tipping it full again. His hand was beginning to waver as he held the bottle aloft. “I’m used to that kind of intensity going along with, you know, _love_ stuff, so I found myself just feeling confused a lot of the time, like I was getting mixed signals or something.”  
Gwendolyn shook her head. “I’m sorry, Bill. I should’ve realized she hadn’t broken her pattern.”  
Bill patted her clumsily on the shoulder before refilling her glass. “No, no, not your fault. I had fun,” he shrugged, taking another drink. “And learned a few things along the way.”  
Gwendolyn giggled into her glass. “Oh, I bet you did…”  
Bill giggled, tipping the last of the second bottle into his glass before standing up, swaying a bit, and heading to the kitchen to grab the third. He refilled both their glasses as he sat back down.  
“Yeah…pretty sure after having her here my neighbors hate me,” he giggled.  
Gwendolyn threw back her head and laughed. “Yeah, she’s a LOUD one, isn’t she?”  
Bill laughed and nodded. “Seriously. Determined to wake the dead, that one.”   
They collapsed into laughter, wiping tears away from their eyes. “Whew, it’s not even two in the afternoon and I am _drunk_ ,” Bill chuckled, blinking his eyes rapidly.  
Gwendolyn nodded slowly. “You’re telling me. I should’ve had lunch.” Bill agreed. “You’re okay though?” Gwendolyn swayed, putting her hand on his shoulder and laying her head back on the couch.  
Bill nodded, twisting his head to look at her. “Yeah, I think I am. Thank you for all of this. Cookies, wine, talking. You’re really sweet, you know?”  
Gwendolyn hummed, looking back at him. Their eyes met, struggling to bring one another into focus but staring intensely. Bill leaned forward, clumsily pressing his lips against hers and for a moment their tongues wrapped around one another, heat building. Then his hand slid up and gently brushed her left breast. Instantly she pulled away, standing up, having to steady herself against the wall for a moment as the room spun.  
“I need to leave,” she said, attempting to make her way toward the door.  
“Shit, Gwen, I’m sorry, I—“ Bill started, standing up and nearly losing his balance but managing to stay aloft.  
“No, just forget it. Let’s forget about it,” she said, shaking her head, then immediately regretting doing so. “Can you get my coat?”  
“Yeah, uh…yeah,” Bill said, rummaging in the closet and handing it to her. “I’m really sorry,” he said again, unlocking the door and opening it to let her out.  
“It’s…yeah, me too,” she said and she hurried down the stairs. The frosty winter air hit her face, sobering her up almost as much as the events of the past few moments. Hailing a cab and jumping inside, she fought the urge to vomit the whole way home, unsure if it was because of the wine on an empty stomach or horror at her own actions. She ran upstairs and knelt in the bathroom, sick until she was as empty as she felt in her heart. No matter what she told herself she couldn’t deny the fact that she’d kissed him back. She hadn’t pulled back right away. Of course it would be easy to blame the alcohol, but it wasn’t that simple. It wasn’t an excuse, and there was that small voice in the back of her mind that mockingly jeered that she’d always had an attraction to Bill, whether she wanted to admit it or not.  
Stepping into the shower and letting the hot water pour over her, she scrubbed hard, willing the memory of Bill’s lips away from her mind. Contemplating whether or not she should tell Conan brought a sharp pain to her chest. What if she told him and he left her? What if she didn’t say anything, but Bill did? She didn’t think the latter was likely, but the thought of keeping a secret like this from Conan made her ache. Screaming, she slapped the shower wall hard, the tears coming hot down her cheeks, obscured by the rivulets of water descending on her from the shower head. Gwendolyn stayed in until she grew pruny, but she still hadn’t solved anything. She stepped out and toweled off, sitting on the edge of her bed wrapped in the towel for a long time, just staring.   
Eventually she got up and dressed, beginning dinner, determined to make things look normal. Conan strolled in around 6:30 and wrapped his arms around her waist, giving her a kiss on the cheek.   
“Hey hun, how was your day?”  
“Good,” she responded. Her voice sounded unnatural in her ears and she hoped he couldn’t hear it.  
“Did you end up going over to Bill’s?” He asked, swaying her a bit. She nodded. “Did he like the cookies? How’s he doing?”  
“Yeah, yeah, I think he’ll be okay,” she said. “There’s extras in the Tupperware over there,” she gestured to the counter.  
“Ooh,” Conan exclaimed, popping open the container and extracting a cookie before promptly popping it into his mouth. “Delicious,” he said, his voice muffled by a mouthful of chocolate chip.  
Gwendolyn forced a smile. “Sit down, stir fry is ready.”  
They sat down at the table and began to eat. “How was your day?” She asked, pushing her food around. She really wasn’t hungry but she supposed she’d have to at least pretend to eat.  
“Pretty good, actually. Will Arnett was on, and he’s always a lot of fun,” Conan said, popping a piece of chicken in his mouth. “And we had a good audience, which always helps.”  
Gwendolyn nodded, lifting a piece of broccoli and half-heartedly putting it in her mouth.  
Conan looked at her curiously. “Is everything okay?” He asked, chewing. “You seem a little down or something.”  
She looked up at him, heart beating fast. “Yeah, yeah. I just…had to kill off a character today,” she lied. “So I’m in kind of a mournful headspace still.”  
“Ah,” Conan nodded. “Well, don’t tell me who. I want to be surprised when I read it.” Gwendolyn nodded. “So what do you think about next week?” He asked.  
“Next week?” She asked, confused.  
“Yeah, Thanksgiving? Do you want to come to Brookline? Or is the idea of meeting all the O’Brien’s just a bit much?” He asked with a smile.  
She managed half a chuckle. “No, no I don’t mind going. I mean, if you’re okay with it.”  
Conan nodded. “Yeah, I want you to come. They’re a lot to deal with, of course, and there’s a lot of us, but I think it’ll be good.”  
Gwendolyn smiled. “So will we be staying at your parents house or…?”  
Conan shook his head. “No, they don’t really have the room. We’ll get a hotel room nearby.”  
She nodded. “Good, I think that’s better.”  
Conan opened his eyes wide and tilted his head. “Trust me. Way better,” he chewed a water chestnut contemplatively for a moment, looking at her. “There’s something I’ve been meaning to ask you.”  
“Oh yeah?”  
“Yeah, I mean now that you’ll be meeting my family and all. Back on our first date you mentioned you don’t really like to talk about yours and we’ve never, well, you never really brought it up again, and I haven’t wanted to pry. But I’ll admit I’m curious,” he said. “You never talk about them.”  
Gwendolyn sighed. “Well, I guess it’s been more than long enough,” she began. “I just don’t like talking about them because, well, because it’s not a pleasant story.” Conan nodded silently and she continued. “First, my mother, well she died when I was six. She…she killed herself, actually…”  
“Oh, I’m so sorry,” Conan said, reaching across the table to take her hand.  
She shook her head. “It’s okay. I don’t remember her at all. I just blocked it all out. Her and my dad were divorced a year or so before it happened. My dad, he’s a drunk and an addict. Not a mean guy, but just neglectful. I have one brother and he’s, well…he’s a monster and he’s in prison, last I heard, at least. He strangled his girlfriend. He didn’t kill her, thankfully, but of course he’s doing time for it, as he should. He hasn’t changed much since we were kids…” She swallowed hard, turning her hand over to interlace her fingers with Conan’s.   
He was quiet for a while, slowly rubbing her hand. “Wow…you must’ve felt so alone growing up.”  
Gwendolyn nodded. “Yeah…honestly I think that’s at least half of the reason why I write. I had to create these fantasy worlds to hide in because reality was excruciating. Eventually I became pretty good at it.” She stared hard at the table. She didn’t want to look at Conan’s eyes, didn’t want to see the sadness there, the pity that was so familiar every time she shared her story. Eventually she broke and looked up and what she saw instead was his face beaming with pride.   
“Damn, you are impressive,” he said, shaking his head. “The fact that you made it this far with so little support, wow.”  
“Thank you,” she murmured softly, biting the inside of her cheek to keep from crying. Conan could see her about to break and he stood up and walked to her side of the table, gathering her into his arms.   
“Come here,” he whispered, holding her tight. A few renegade tears squeezed loose from between her eyelashes and fell onto his shoulder as he rocked her in his arms. “I am amazed and grateful for all the hard work it took for you to be here,” Conan said, his voice growing thick. “And, um…” his voice trembled. “It means a lot to me that you never gave up, because otherwise you wouldn’t be with me.”  
Gwendolyn began gently sobbing into his chest, crying for some reasons she couldn’t say, and he held her close, tears falling into her hair. As their crying came to an end they slowly separated, feeling weary and drained. They gave up on finishing the rest of their dinner and mutually decided to head to bed. Quickly putting things away, they climbed into bed together silently, holding one another and turning out the lights, grateful for caring arms to cradle one another in their dreams.


	4. IV

The next week as they drove over the snowy roads to Brookline, Gwendolyn felt herself growing nervous. She wanted to make a good impression on Conan’s family, but she wasn’t entirely sure what to expect. When they pulled up to the pleasant suburban home her heart was beating fast, and as the door opened the first thing she noticed was the sheer _volume_ of people packed into the home. Having come from a small and distant family, she was not prepared for this large Irish brood, particularly since most of them were exceptionally tall.  
“Hello Pigeon Pie!” An old woman who could only be Conan’s mother said as she reached up to give him a kiss on the cheek. Gwendolyn chuckled internally at her pet name for him and made a mental note to tease him about it later as she was introduced around to his parents, five brothers and sisters, and various cousins, nieces, and nephews.  
Grateful for her cooking skills, Gwendolyn offered to help the women in the kitchen and was put in charge of the mashed potatoes. Both Conan’s mother and father asked her if she was Irish, looking at her hair, and when she said she was at least a little, but she didn’t know how much, they nodded approvingly.  
With surprising speed the meal was ready and they all sat around the table. It seemed twenty conversations were going at once, and Gwendolyn tried to politely contribute where she could. One of Conan’s cousins turned out to be a diehard fan of her book and desperately tried to press her for spoilers about the next installment, and though she was flattered, she did not relent.   
About halfway through the meal Conan’s mother made a comment about “hearing wedding bells” which made the two of them blush and Conan whined “ _Mom_!” But overall everything went smoothly and before long they were saying their goodbyes and heading back to the hotel.   
When they reached their room they flopped back onto the bed, full and exhausted.   
“Well, that went okay,” Conan said, turning his head to face her.   
Gwendolyn nodded. “Yeah, yeah, better than I expected,” she said. “Weird, though.”  
Conan scrunched his brow. “Weird, how?”   
“Well, you all actually _care_ about each other. Like you talk, and know things about each other. I’ve just…never been around that before, really,” she said, shaking her head. “Just not used to it.”   
Conan pushed back her hair and kissed her cheek, saying nothing. Eventually they both rolled into a sitting position and stood up, getting out of their fancy clothes and changing into pajamas. Before Gwendolyn could pull her bottoms on, however, Conan grabbed her and tossed her back onto the bed, taking her mouth in his. “Gotta work off that meal,” he murmured into her lips. She smiled against him as he reached down and removed her underwear, slithering out of his boxers as he went. His hand worked away between her thighs, coaxing her until she was wet and desperate, moaning affectionately in his ear. He slid his turgid cock inside of her, thrusting gently a few times before flipping over, allowing her to ride him and dictate the pace. She rocked languidly, taking him into herself with care, and he put one hand between them to finger her in time with their motions. Increasing speed gradually, she began pounding herself down onto him, moans escaping her with each descent of her pelvis as he burrowed inside of her. Conan thrust into her willingly, digging his heels deep into the bed for leverage and arching his hips high, feeling her constrict around his cock as her orgasm approached. Falling over the edge, Gwendolyn leaned forward, placing her hands on his shoulders and leaning forward as she ground her hips into him hard and fast. Conan followed soon after, hips shuttering forth erratically as he came, groaning long and loud as he dug his fingers into the flesh of her thighs.  
When her trembling ceased Gwendolyn rolled off, brushing her hair away from her face. Then she started laughing.  
“What’s funny?” Conan asked, still trying to catch his breath.  
Still giggling. “ _Pigeon pie!_ ” She cried, carrying over into helpless peals of laughter.  
Conan rolled his eyes. “Oh my…you had to bring that up _now_?”  
She nodded. “I-I’m sorry. It was just too good.”  
He pinched her playfully. Once she composed herself they got ready for bed and turned out the lights. Snow fell outside of the hotel windows, muffling the noises of the world as they drifted into warm dreams.

——-  
On the drive home the next day they had to go at a glacial pace due to the hazardous winter roads. Gwendolyn was grateful to have Conan behind the wheel, as she wasn’t the most confident driver, but he didn’t seem bothered.  
About halfway through their drive he turned down the radio. “Hey, so, I wanted to ask you something.”  
“Sure, what’s up?” She said, taking off her coat now that the car was warming up.  
“So things are going pretty well, right?” He asked, tapping the wheel.  
“Things?”   
He gestured back and forth between the two of them with one hand. “With us.”  
“Oh, yeah. Yeah, I’d say so,” she said hesitantly.   
“Well, I was thinking, uh…since we’re spending mostly every night together anyway…and spending so much on cabs and all…” he paused to sniff. “Maybe we should just, you know, move in together.”  
Gwendolyn looked at him, blinking. “Yeah? You think so?”  
“Yeah…I mean…do you?” He asked, watching the road.  
She nodded. “Yeah, yeah. I think we’re, you know, ready,” she said. “I think we know by now that we can get by without driving each other crazy.”  
Conan nodded. “Yeah, I think so. Though I think we should look for a new place together, instead of moving into either your place or mine.”  
“Yeah,” Gwendolyn nodded. “I think that’s smart.”  
“Good,” Conan smiled. “Well, I’ll make some calls next week.”  
“Great,” Gwendolyn nodded before leaning over to kiss him on the cheek, excited. “Have you ever lived with anyone before?”  
“Nope,” Conan laughed. “First time. You?”  
“Same.”  
“Well, we’ll figure it out together then,” he said, slowing down to make a tricky turn.   
Gwendolyn nodded and smiled. Inching their way back to New York they made it to the city safely, unloading the car and spending the rest of the day relaxing and decompressing from the trip.  
—-

  
Snow fell in sheets outside the windows as they sat in Conan’s apartment, both reading on the couch.   
“So what’s the plan for Christmas?” Gwendolyn asked, looking at him over the cover of her book.   
“Hmm?”  
“Are we going to your parent’s place?”  
Conan shrugged. “I dunno. I thought maybe we’d do something low-key,” he suggested. “You know, just us.”  
Gwendolyn nodded. “Sounds nice.”  
They went back to reading, and as the day approached they purchased gifts and Gwendolyn enjoyed having Conan around more during his time off work, though he turned stir crazy rather quickly and she found herself inventing fake tasks to keep him busy.  
On Christmas morning they exchanged presents. She gave Conan a personalized guitar strap and he gave her an antique hair clip that belonged to his grandmother. Gwendolyn made roast pork with potatoes and carrots and they spent a quiet night in, enjoying one another’s company.  
—-

  
A couple of months later they moved into a four-bedroom apartment uptown. Moving in New York in late February wasn’t exactly the most pleasant experience, but they made it work, and once they had the majority of the boxes unpacked they collapsed on the couch, exhausted.  
“Want to order some delivery?” Conan suggested.  
Gwendolyn nodded, grateful he’d mentioned it, as she was not up to cooking. He called their favorite Thai place and not long after they were hunched over containers, sitting at the kitchen table, eating ravenously. Once finished, they sat back, satisfied. “Ugh, I should go make the bed,” Gwendolyn stood up reluctantly. They’d ordered a new king bed and it was delivered that morning.   
“I’ll help,” Conan wiped his mouth and followed her. They removed the plastic from the mattress and found the box containing their sheets and blankets, each grabbing a side as they began assembling.   
Fluffing and placing the pillows, Gwendolyn said, “There we go,” and looked at it admiringly. Conan came around the side of the bed, snuck up behind her, and full on lifted her into the air, slamming her into the bed.  
“Hey!” She objected, limbs flailing.  
“What?” He said, jumping in after her. “We gotta break this thing in.” He smiled at her and pulled her shirt over her head, kissing her as he went. They finished undressing one another and he kissed his way down her body, gliding his tongue down her abdomen and between her thighs, gently kissing her opening before parting her lips with his fingers, lapping against her with the flat of his tongue. He inserted his fingers, stroking her inside as he began swirling her clit. She moaned and rose to meet his face, crying out as her first orgasm caused her to clench around his hand. He did not relent, however, but pressed on, starting to suck on her clit, burying his nose into her as he heard her screams mount above him. Conan didn’t stop until he made her cum twice more, thrashing and yelling as she pounded her fists into the fresh bedding. Rising up to mount her, Conan slid his cock inside of her and her back arched underneath him. He lifted both of her legs up over his shoulders, pounding into her, rocking the backboard of their new bed into the wall. It was a good thing they hadn’t taken the time to hang any photos yet, because he hammered into her with such feverish intensity they would’ve knocked them all down. Gwendolyn placed her hands behind her head, screaming as she came for a fourth time while Conan quickened his pace, driving deep inside of her, feeling the walls of her contract and flutter against his tender cock. His movements were rising out of control when they both heard a loud pounding on the door.  
“Open up! Police!”  
Conan froze. Looked toward the door. Then down toward Gwendolyn. Then back to the door.  
“Uh…be right there!” He called out awkwardly. He pulled out and frantically scrambled around the floor of the bedroom, pulling on his clothes, accidentally pulling on his jeans backward at first and having to take them off and try a second time. Willing his erection to go down as he approached the door he took a deep breath and opened it, exposing two humorless, hulking officers.  
“Uh…what seems to be the problem, officers?” He asked, still trying to regulate his breath.  
“Sir, we got a call about a domestic disturbance at this address,” they said.   
Conan looked confused. “A disturbance?”  
“Yes, sir. Someone called 911 saying they heard a woman screaming in here. Are you in there alone, sir?”  
“No, uh…no, my girlfriend is here,” Conan knew it would be a huge mistake to start laughing, and he bit his lip. “Hey Gwen,” he called back into the apartment. ”Could you come here?”  
Gwendolyn emerged, looking flushed and bedraggled in one of his t-shirts and whatever bottoms she’d managed to scrounge in a hurry. “Hello, officers…” she said, coming to stand at Conan’s side.  
“Ma’am, we’ve had a report that there was a woman screaming at this address tonight. Do you know anything about that?”   
Gwendolyn went deeply red. “Oh, uh…yeah…that was, um…me.”  
“Is there a problem here?” The left officer asked, looking Conan up and down suspiciously.  
“No! No,” Gwendolyn said, frantically waving her hands. “We were um, well…we were you know…in bed, and um, I was doing the screaming there…so…no, no problem.”  
The officers exchanged a glance, the right one raising his eyebrow, nodding. “Alright, well if you don’t mind, can I talk to you in the hallway for a minute, ma’am?”  
Gwendolyn nodded and followed him outside while the other officer stayed in the apartment with Conan.  
“Ma’am, are you feeling safe in your relationship?” The officer asked under his breath, pulling her aside.  
“Yes, sir. Very much.”  
“So you’re sure you’re okay?”  
“Yeah, I mean, a little embarrassed…but fine.”  
The officer nodded. “Okay. Glad to hear. As you can imagine, most of these calls don’t go like this.”  
Gwendolyn nodded solemnly and turned to head back to the apartment.  
“Well, you two have a good night,” the officer on the left said. “Just…maybe try to keep it down, okay?”  
Conan blushed and rubbed the back of his head, nodding. “Sure, officer.”  
“Love your show, by the way,” said the officer on the right.  
“Thank you,” Conan said with a half smile. “Have a good night.” They gave a little wave and Conan closed the door behind them, letting out a long breath before he and Gwendolyn’s eyes met and they burst out laughing, collapsing against one another and sliding to the floor.  
“Welcome to the neighborhood,” Conan laughed, wiping away tears.  
Gwendolyn nodded. “Think we made a good first impression?”  
Once they were able to compose themselves they stood up and went back to bed. Gwendolyn took Conan into her mouth, finishing him off quickly as she sucked thirstily on his cock. They settled into their new bed, in their new apartment, smiling to themselves about the interesting turn of events on their first night in their new home.  
***

  
Two days later Conan was walking through the office and he noticed some snickering as he passed. Writing it off as self-conscious paranoia, he went about his day without giving it a second thought. He was sitting at his desk doing some paperwork when his producer Jeff came in, holding something behind his back.  
“Hey Jeff, what’s up?” He asked.  
Jeff rocked back and forth on his toes, not making eye contact. “You haven’t, uh, seen the _Daily Mail,_ today, have you?”  
“Come on, man, you know I don’t read that trash,” Conan said, shaking his head and looking back down at his paperwork.  
“Well…” Jeff said, pulling the periodical from behind his back. “You, uh, might want to take a look at it this time…” He held it out in Conan’s direction as if it were radioactive. Conan snatched it reluctantly and scanned the cover for a few seconds before his eyes went wide.  
“Oh _no_ …” he groaned, looking at the headline.

  
**BONIN’ CONAN: LATE NITE QUIPSTER SEXCAPADE INTERRUPTED BY CALL TO COPS**

  
Conan ripped it open to the page indicated on the cover and read the whole sensationalized story, growing queasier with each word. “Shit, I gotta call Gwen,” he said, half to himself. He handed the paper back to Jeff and rubbed his face.   
Jeff tentatively took the paper and hid it behind his back again, as if that would make the story itself disappear. “I’m sorry, I thought you should know.”  
Conan nodded. “Yeah, thanks. I’ll…I’ll deal with it. Thanks.”  
Jeff nodded and left. Conan picked up his phone and called Gwendolyn, who answered with a sunny, “Hey!”  
“Hey, hun,” he started, biting his lip. “So…there’s some news, um, and it’s not great…”  
“Oh, no, what’s wrong?” She asked.  
“Well, uh, you know the other night when the cops came to the door?”  
Gwendolyn chuckled throatily. “How could I forget?”  
“Well, uh, turns out someone went to the tabloids, and um, the story is in the Daily Mail today.”  
“Oh…oh _no_ …” she groaned. “I’m so sorry!”  
“No, no don’t apologize, it’s not your fault,” Conan said, shaking his head.  
“Well, I mean, it kind of is a _little_ bit…” she responded. “If I had been quieter…”  
“Well, by that logic,” Conan said. “Technically, you could say it’s my fault.”  
Gwendolyn laughed. “Oh wow, damn. So, what’re you going to do? I mean, people are going to be talking about it. Are you going to address it on the show?”  
“Honestly, I haven’t thought that far ahead yet,” Conan said. ”I only heard about it now and I’m still digesting it. How about we talk it over tonight?”  
“Sounds good,” she responded. “I’ll see you then.”  
“Okay, love you.”  
“Love you, too. Bye.”  
Conan went back to his paperwork, and after finishing up strode down the hallway to the writer’s room to go over the bits for that night’s show. As soon as he opened the door, however, he was greeted by a round of applause and a smattering of wolf whistles.   
“Alright, alright,” he said, spreading his hands in an appeasing gesture. “Enough of that.”   
The room slowly rolled to a quiet and one of the gutsier writers piped up, “So Conan, are the headlines true?”  
Conan laughed. “I’m discussing it with Gwen tonight, and until after that, I’m sure as hell not talking about it with any of you creeps.” They laughed and went about their business. The show went smoothly, and after wrapping he stood outside trying to catch a cab and was approached by a fan.  
“Hey, would you mind giving me an autograph?” The young woman asked.  
“Sure” Conan said, turning to her. Then he saw she was holding out the dreaded tabloid for him to sign. He pulled a face. “Do you have anything else I could sign? Anything but that, please.”  
She laughed a little and pulled a small notebook out of her purse, which he happily signed instead, and she went on her way. A cab rolled up and he headed home. When he got to the apartment Gwendolyn was sitting in front of her easel working on a painting.  
“I’ll be in in a minute, let me just get to a good stopping point,” she called.  
“Okay,” he called back, grabbing a book and sitting on the couch. About ten minutes later she emerged and joined him.  
“So, I read it,” she said, sitting down with one foot curled up underneath her. “At least in essence, it’s true. They didn’t toss in any straight up lies about either of us, as those rags are known to do.”  
Conan nodded. “Silver linings, I guess.”  
“So,” she began. “Did you want to talk about it on the air?”  
Conan tipped his head back and forth. “I don’t know. What do you think about it?”  
“Well,” she looked up, counting on her fingers. “On the one hand, yes, it is really personal. But it is already out there. We can’t stop it now. And even I can see the comedic potential here. So maybe we, I don’t know, steer into the skid?”  
Conan leaned back, tapping his chin. “Hmm, well, in that case, would you be willing to come on to the show? To talk about it?”  
“Oh,” Gwendolyn looked taken aback, thinking for a moment. “Yeah…yeah I think I could do that.”  
Conan nodded. “There might be something here…”  
***

  
The next day Gwendolyn accompanied Conan to work, strolling in with him to the writer’s room to brainstorm. Later, they both sat together getting their makeup done, smiling at one another in the mirror.  
“You ready?” He asked, trying not to move his lips too much as his face was powdered.  
Gwendolyn gave a half nod, attempting not to move her head too much as the woman behind her curled her hair.  
Conan went out first and Gwendolyn stood back stage, twisting her hands together and pacing on the spot as she heard him introduce her.  
“Alright everybody, some of you may have heard I made headlines recently, there it is,” they showed a picture of the cover of the _Daily Mail,_ people woo’ed and laughed. “Yeah, alright, alright. Well, here to talk about it with us tonight is _New York Times_ best selling author, _Hugo Award_ winner, and by far her greatest accomplishment—my girlfriend—Gwendolyn Greene!”  
She came walking out to the music, waving, giving Andy a hug before embracing Conan and giving him a quick kiss, which garnered a couple of whistles from the crowd, before taking a seat next to him.  
“Now, Gwen, thanks for coming on to clear this up. Are you ready to talk about this?” He asked, gesturing to her.  
She nodded. “Yes, Conan. I am.”  
Instantly the house lights dimmed and a spotlight shone down on her. “Now then ma’am,” Conan began, affecting an old-timey detective voice. “Where were you on the night of February the 28th?”  
“I was in bed with you,” Gwendolyn responded seriously.  
“And what were you doing?”  
Gwendolyn fought the urge to crack. “Engaging In consensual adult activities.” The crowd laughed and woo’ed.  
“And can you tell the court what happened next?”  
“Well, I’m a writer so I’m going to put this as delicately as I can…” she began, tapping the arm of the chair. “Due to the…quality of your…ministrations…um…” she suppressed a giggle, and could feel her face warming as the audience laughed. She began to cover her face and laugh.  
Conan dropped the voice for a moment. “No, no, no,” he said, laughing. “You don’t get to hide behind your hands and laugh. You agreed to this, we’re stuck out here together now.” Gwendolyn laughed harder before taking a moment to compose herself.   
“Yes, so, as I was saying, the, uh, decibel level of my reaction to these aforementioned ministrations provoked concern about my well-being amongst our neighbors, prompting them to inform the authorities.”  
“Very well, and—“   
“Wait, wait, wait,” Andy interrupted him. “If it pleases the court, I have a question.”  
“Prrroceed,” Conan said, rolling his ‘r’ dramatically.  
“So you’re saying, ma’am, that you were screaming _so_ loudly that your neighbors feared for your life?”  
Gwendolyn nodded. “That’s correct, sir.”  
Andy stood and walked over to Conan, enthusiastically shaking his hand. “Well done.”  
Conan broke, laughing and running a hand over his face as Andy returned to his seat. The audience howled as he took a moment to compose himself.  
“If you would,” he suppressed a giggle. “Continue with what happened next, ma’am.”  
“Officers of the law arrived at the door to investigate.”  
“And what did you do?” Conan trilled, his old-timely accent beyond ridiculous.  
“They inquired as to whether I was in any danger, and I informed them I was not, and the officers left.”  
Conan narrowed his eyes as if considering deeply. “Hmm, I see. And then what did you do?”  
“Oh, honey, then we went _back to bed_.” The audience lost it and Conan put his head down on the desk, pounding his fist.   
When he emerged, red faced and laughing, he said, “Jeff, remind me to tell my mother to skip this episode.”  
Gwendolyn laughed, covering her face. “Well, there you have it folks,” Conan said, composing himself. “Now that we’ve put this matter to bed,” he chuckled. “If you see me on the street, please, please, do not ask me to sign this story and if frat guys could stop yelling “BONIN’ CONAN!”at me everywhere I go, that would be great,” he shook his head. “Now when we come back from the break, we’ll have Jim Gaffigan joining us, stick around!”  
They went to commercial and Conan leaned over to kiss Gwendolyn on the forehead before pressing his head to hers, breaking into mutual laughter.  
“That was pretty good,” he said.  
She nodded. “Yeah, it was fun. I’m glad we did it.”  
Standing up to move over and sit next to Andy, Gwendolyn enjoyed the rest of the show, though it was odd watching it from the perspective of the guest couch. After they wrapped they hung out and chatted with Andy and Jim for a bit, enjoying a few laughs before scrubbing off their makeup and heading home. 


	5. V

A few weeks later they were in bed reading before going to sleep when Conan set down his book and looked over at her.   
“So…you’ve been with men and women, right?”  
“Mmhmm,” she responded, not looking up from the page. “And one trans woman, but we only dated for a couple of months.”  
“Oh yeah?” He asked.  
Gwendolyn nodded. “Yeah, she was just starting her hormone treatment and she found as she went along that she became more and more attracted to men,” she said. “Apparently it’s not uncommon for your orientation to waver with the hormones. We tried to make it work for a bit, but eventually decided we made better friends than lovers.”  
Conan nodded. “Interesting. So…how many people have you been with?”  
Gwendolyn laid her book on her chest and looked over at him over her reading glasses. “Why do you want to know?”  
“Just curious.”  
“No.”  
“No?” Conan asked.  
“No, you’re not just curious. There’s a motive behind that question,” she said, adjusting herself on the bed. “If you can give me a good reason why you want to know, I’ll tell you, but you’re not ‘just curious’.”  
“Fair enough,” Conan held out his hands. “I guess I…” he made a gesture as though he were grasping something invisible in the air. “…worry that with all of your…experience that maybe, someday, you’ll grow bored with me. So I get concerned.”  
Gwendolyn folded her book and set it on the bedside table, turning to face him on the bed. “You’re looking at it from the wrong angle,” she started. “Can’t you see that I had to go through all of that experience to see what I didn’t want? And now I’ve found everything I’ve been looking for in you?” She reached over and grabbed his hand.  
Conan nodded, smiling. “Okay, okay, I guess that makes sense.”  
She smiled, reaching for her book.   
“So…how many?”  
Gwendolyn sighed. “You’re sure you really want this information?”  
Conan nodded.  
“Okay,” she tilted her head. “Well I’ve been with eight women, including Michelle, who’s trans,” she took a breath, averting her eyes. “And thirty-six men.”   
“Thirty-six,” Conan said flatly.   
“Yes.”  
“Does that include me?”  
“You’re thirty-seven,” she responded.  
“ _I’m thirty-seven,_ ” Conan raised his voice, standing up from the bed and running his hands through his hair.  
“Conan…” Gwendolyn said softly, but he didn’t seem to hear her as he began pacing the room.  
“Thirty- _seven_ , how is that possible?!” He gestured wildly, his pacing increasing.  
“Conan, calm down…” Gwendolyn stood up and held out her hands in an appeasing gesture, but he wasn’t listening to her.  
“Thirty-seven, that’s…that’s…” he couldn’t look at her.  
“To be fair,” she said calmly. “I probably got started earlier than you did.”  
“When?!” He was practically screeching. “1972?!”   
“Hey!” Gwendolyn yelled back, but he was unfazed.  
“I mean, seriously Gwen, what the hell did you do?!” He yelled, rounding on her. “Spread your legs and hang a shingle outside of the door that said ‘Open for Business’?”  
He didn’t see her hand coming but he sure as hell felt it. She’d thrown all her weight behind the slap and when he turned back to face her, tears were streaming down her face.  
“Fuck. You,” Turning from him in disgust she left the room, stepping into a pair of shoes and hastily grabbing her purse and a coat.  
“Gwen…Gwen, wait, I—“ he called after her.  
But she just screamed at him over her shoulder. “FUCK OFF!” And slammed the door behind her. Conan slammed his forehead against the closed door, cursing under his breath, nauseous at his own actions.  
Bleary-eyed, Gwendolyn didn’t know where she was going, just walking wherever her feet carried her and grateful that it wasn’t cold enough to freeze the tears to her face. When her head began to clear a bit she went into the first bar she came across, choosing a stool at the far end and ordering a vodka tonic, which she promptly downed. Perhaps noticing her red eyes, the matronly barmaid refilled her glass and said, “This one’s on me, hun.” Gwendolyn thanked her and began sipping it down, anxious to feel anything but this permeating dread, anger, and profound sadness.  
Her third refill arrived when she heard a quiet “Hey,” at her shoulder, surprising her into spilling the drink down the front of her shirt. She turned and saw Bill Hader standing next to her.  
“Bill! Hey, what’re you doing here?” She asked, realizing after that it was kind of a rude question.  
“Oh, this is one of my regular places,” he gestured around the bar. “How about you? Is Conan here?” He looked around.  
Gwendolyn swallowed past the sharp pain in her throat. “No, um,” she gripped her glass tight, determined to maintain composure. “We had a fight, actually.”  
“Oh…oh, I’m sorry,” Bill said quietly. He took a sip of his beer, then swirled it idly for a moment. “Do you want to talk about it?”  
She looked over at him. “You really want to hear about it?”  
Bill shrugged, sitting on the empty stool next to hers. “Only if you want to talk.”  
Gwendolyn nodded, tapping the rim of her glass. “Well,” she began, taking a pull of her straw. “It started with Conan asking how many partners I’ve had,” she gestured to the bar maid for a refill. “And I knew, _I knew_ , it was trouble. But I told him and…” she sighed deeply. “I mean, he lost it, Bill. He freaked out.”  
Bill nodded, silent.  
Gwendolyn’s refill arrived and she drank down half of it. “And I just…” she tried to hold back, but her voice became watery and tears rimmed her eyes. “I just thought that he loved me enough that a number wouldn’t matter, you know?” She turned away and wiped her face. Taking a tremulous breath to compose herself and looking upward to blink the tears back into her eyes, she shook her head and finished her drink, ordering another.  
“Man, I’m sorry. That’s rough,” Bill said.  
Gwendolyn nodded. They sat in silence for a while and she finished her drink, having lost count of how many she had. “Shit, I gotta find a hotel,” she said. Her tongue seemed too big for her mouth as she reached into her purse and pulled out a few crumpled bills, placing them on the bar. Attempting to get off her stool, she slid off, stumbling, and Bill caught her.  
“Alright, okay there,” he said. “Take it easy.”  
“I-I’m fine,” she slurred. “I’ll be okay.”  
“Okay, come on,” Bill said, hooking one arm underneath hers and guiding her out of the bar. Walking as though they were competing in a three-legged race and losing, badly, they made their way back to his apartment. Bill laid her down in his bed, taking off her coat and shoes and allowing her to flop on top of the covers.  
“Okay, Gwen?” He said, speaking as if he were explaining something simple to a toddler. She grunted a little. “I’m going to go sleep on the couch. I put a bucket on the floor here in case you get sick and there’s a glass of water on the night stand for when you wake up, okay?”  
She mumbled something that might’ve been thank you. Bill took the free pillow from the other side of the bed and looked back at her sprawled over his bed for a moment before turning out the lights and heading to the living room.  
—-  
“Ughhh,” Gwendolyn groaned, rolling over and blinking blearily against the light streaming into the room. She sat up and instantly regretted it as the room sloshed about. Raising a hand to her head to steady herself, she realized she had no idea where she was. Seeing the glass of water on the table she grasped it gratefully and began to sip, and as she did some memories of the night before flooded back. _Bill. I’m in Bill’s apartment_. Looking over her shoulder she was relieved to see she was alone in the bed. She looked down and saw that she still had all her clothes on. A good sign. Slowly she worked herself to a standing position and shuffled her way toward the kitchen.  
Bill stood in front of the sink, blowing steam off a cup of coffee. “Hey,” he said. Gwendolyn nodded, one eye open. “Want coffee?”  
She shook her head. “I’ll stick with water,” she held the glass aloft and sat in the chair across from him.  
“Do you think you can eat something?” He asked.  
She pondered for a minute. “Toast? Maybe?”  
Bill nodded and turned around, dropping two slices in the toaster.  
“Hey Bill…we didn’t…I mean, nothing happened, right?” Gwendolyn asked, gesturing between the two of them.  
Bill held up his hands. “No, not at all,” he took a sip of coffee. “I just didn’t think you could safely find your way to a hotel.”  
“You’re probably right,” Gwendolyn nodded. “You didn’t have to give up your bed though…”  
Bill shrugged. “It’s no big deal. I have a comfortable couch.”  
The toast popped up and Bill put it on a plate, handing it to her. Biting into it tentatively, she chewed and swallowed as if she was doing so for the first time, hoping her stomach wouldn’t reject it.  
“Have you decided what you’re going to do? About…” Bill asked, eyes flicking downward.  
He didn’t need to finish. Gwendolyn knew what he meant. She sighed. “I guess I’ll have to go back and face him,” she said, picking at her toast. “I don’t know what I’m going to say. I don’t think I’ll know until I see him.”  
Bill nodded.  
“But, um, if it ever comes up…” Gwendolyn tapped her thumb on the edge of her plate. “Maybe it’d be best to say I spent the night in a hotel.”  
They locked eyes for a moment and held each other’s gaze.  
Bill swallowed, nodding. “Yeah, sure, that…that makes sense.”  
Gwendolyn finished her toast and brushed off her fingers over the plate. “Well, I suppose I’ll head out.”  
“Okay,” Bill said. “Good luck.” He gave a half smile.  
“Thanks. And thanks for, you know, everything,” she pulled on her coat and stepped into her shoes. Gwendolyn hesitated for a moment at the door, standing awkwardly for a moment before finally deciding to lean in for a hug. Bill wrapped his arms around her and squeezed her tighter than he intended, turning his face into her hair and enjoying the lingering feeling of her body around him. When they parted they said their goodbyes quickly, not making eye contact, and Bill closed the door behind her, fingers lingering on the doorknob.  
When Gwendolyn got back to the apartment, Conan was on the couch and he sprang up as soon as she entered, walking to meet her in the kitchen.  
“Hey…” he said sheepishly, putting his hands in his pockets.   
Gwendolyn nodded, taking off her coat and shoes and setting down her purse.  
“I’m really glad you came back,” he said.  
She couldn’t look at him. Standing still, arms hanging at her sides, she stared at the floor.  
“Listen, Gwen, I-I’m so sorry…What I said, that was…it was awful, and I didn’t mean it. I was just feeling…insecure and I got stupid and—“  
Gwendolyn held up a hand to stop him. “Let’s sit down,” she said in a voice barely above a whisper. Conan nodded, afraid. He followed her to the couch.   
She cleared her throat. “I want to say a couple of things,” she began, still looking down. Conan nodded, letting her speak. “As angry as I am about what you said,” she picked at a loose thread on the couch cushion. “It hurts more because, um…” she looked to the ceiling, eyes gleaming, and raised a trembling hand to cover her mouth. “Because it means that I’m not the kind of woman you can see spending your life with,” and with that she doubled over into herself, racked with sobs, body shaking with grief as she held her face in her hands.  
“Oh, oh Gwen _no…_ ” Conan said, attempting to wrap himself around her, rubbing his hand over her head and softly rocking her back and forth. “Gwen, no, that’s not true…” his voice grew thick as his own tears began to fall against her shuddering back. “The only future I can see is a life with you,” he held her tighter, willing her to hear his words. “Please, Gwen, _please_ …I’m so sorry…I didn’t mean it,” he shook his head against her. “And it will be one of the greatest regrets of my life that I hurt you like this. Please, please, I love you so much…” he began sobbing, burying his face in her hair and clinging to her desperately.   
After a few minutes they cried themselves out, and unraveled from one another, sniffling. They looked at each other, red-eyed and weary.  
“Can you forgive me?” He asked, rubbing his thumb over her cheekbone.  
She nodded. “And you’re sure…you can live with this?”  
“Don’t give it another thought,” he said. They embraced, breath still hitching from time to time and as they separated Gwendolyn wiped her eyes once again.  
As they made love that night, they fell into one another, raw and vulnerable. They moved together like the tides, rising and falling under the blue moonlight streaming through the windows, crashing against one another in peaceable contentment. As they reached the cliffs of their pleasure, their fingers and bodies intertwined and they jumped together, diving headfirst into the unknown.  
________

Gwendolyn was flipping through the paper when she uttered a gasp.  
“What’s up?” Conan asked, sipping his coffee.  
“ _Hedwig and the Angry Inch_ is showing on Broadway!” She exclaimed, bouncing and clapping.  
Conan looked confused. “Never heard of it.”  
“Oh, it’s my favorite musical,” she smiled. “It’s about a gender-nonconforming East-German rock star whose Jesus freak teen boyfriend steals her music.”  
Conan looked more confused. “Uhhh…what?”  
“Okay, okay,” she held out her hands. “I realize that sounds odd, but the music is beautiful. And Neil Patrick Harris is headlining.”  
“Oh, well,” Conan turned down the corners of his lips appraisingly. “I suppose I could sit through that…”  
“Yay!” Gwendolyn jumped up, kissing him on the cheek. “Thank you! I’ll call and get tickets!” She did a little dance and Conan laughed at her excitement.  
That weekend they got dressed up and went to the theatre, Conan in a sharp black suit with a black and cream tie, and Gwendolyn in a form-fitting burgundy dress.   
“Thanks for coming with me,” she leaned over to him before the show started. “I know this isn’t really your thing. I appreciate it.”  
“No problem,” he squeezed her thigh.   
The show began and Gwendolyn was transfixed, singing along softly from time to time to words she knew by heart. Conan, to his surprise, was pretty entertained. The story was compelling and the music was quite good. And of course Harris was an amazing showman.   
When the show ended, Gwendolyn wiped her eyes and they stood to leave. As they filed out of the theatre with the rest of the audience, she reminisced about her favorite parts.  
“Oh, and _Origin of Love_ is my absolute favorite song. If you ask me, it’s the most romantic song ever written,” she said.  
“Oh yeah?” Conan leaned into her, kissing the top of her head.  
“Definitely,” she stated. “Achingly beautiful.”  
As they went home and got in bed, an idea began to form in Conan’s mind.  
—-  
The next week, Gwendolyn arrived at the studio with Conan’s lunch.  
“Chicken Parmesan,” she said, handing him a container.  
“Mmm, thank you,” Conan said, sitting down and tucking a napkin into his shirt.   
Gwendolyn pulled a chair up to his desk and tucked into a dish of her own. “Things going alright today?”  
He nodded. “Yeah, so far so good,” he twirled his fork. “Why don’t you stick around for the taping?”  
Gwendolyn shook her head. “I should really get back to writing.”  
“Ah, come on,” Conan elbowed her. “You know I like having you in the audience.” He made a fake pouting face and she laughed.  
“Oh, alright, you convinced me,” she sighed. “But if I miss my deadline, I’m telling my publisher to blame you.”   
They hung out for a bit, and when Conan went off to take care of his responsibilities, Gwendolyn chatted with the writers and crew members she’d become friendly with over the past few months. As they got close to filming, she went out to the studio and was directed to a seat in the front row, where she waited quietly for the show to begin.  
Conan came out and Gwendolyn cheered as loud as anyone, appreciating the little wink he gave her before launching into his always hilarious monologue. The skits were excellent, and when they came back from commercial break she realized she didn’t know who the guests were tonight.   
“Now, everybody, you may have noticed we did things a little differently tonight in that we didn’t announce our guests at the top of the show. That’s because our first guest is a surprise for someone in our audience. Tonight we have my girlfriend, Gwendolyn Greene, sitting right there, c’mon, let’s get a camera on her,” he pointed at her and a camera swiveled in her direction. She covered her face, embarrassed.  
“Yes, folks, as per usual I spend my life embarrassing her,” The audience laughed. “Well, my first guest tonight is the extremely talented actor, singer, and entertainer. Known for ‘How I Met Your Mother’ and currently starring on Broadway in ‘Hedwig and the Angry Inch,’ please welcome, Neil Patrick Harris!”  
Neil came walking out, waving to the audience, and shook hands with Andy and Conan before sitting down.   
“Good to see you, Neil, thanks for being here.”  
“Yeah, thanks, Conan. Glad to be here,” Neil said, straightening his lapel.  
“Now Neil,” Conan began. “Gwendolyn and I came to see your show last week and this thing, it’s amazing. It’s quite the production.”  
“Yeah, thank you, it’s the hard work of a lot of people and I’m just so glad to be a part of it and to be able to tell this story on the stage.”  
“Well, so, I called you up the day after and I asked you…I asked if you would do me a favor,” Conan said.  
“Yup.”  
“Because Gwendolyn informs me,” Conan gestured to her. “That _Origin of Love,_ one of the songs from your show, is quote, “the most romantic song ever written.” And so,” he reached behind the desk, pulling out one of his guitars, and the wall to the right of the desk opened to reveal a stool, amplifier, and a couple of microphones. “I spent the week practicing, and you agreed to help me out. You ready?”  
Neil nodded, standing up and following Conan over to the microphone.   
Conan plugged in his guitar. “Now the band is going to help us out a bit here,” Conan said. “Here we go.”   
Conan played and Neil sang, with Conan singing along a little from time to time  
As the song wound to a close and Conan played the final few notes, Gwendolyn clasped her hands to her chest, swelling with gratitude. Unable to help herself, she ran up and placed her hands on either side of his face and kissed him deeply, provoking a frenzied response from the audience.  
“Well folks, there you have it,” Conan chuckled. “Special thanks to Mr. Neil Patrick Harris!” He shook his hand and clapped him on the back. Gwendolyn thanked him as well and they went to commercial.   
“Thank you for that,” Gwendolyn whispered quickly, squeezing Conan’s hand and smiling at him before heading back to her seat. Watching the rest of the show was entertaining and after they wrapped she followed Conan backstage, waiting for him to change and scrub off his makeup so they could head. home.  
“That was really amazing,” she said as they rode home, leaning her head on his shoulder.  
He smiled at her. “Glad you liked it.”  
“I’ll have to think of some way to pay you back.”  
Conan shook his head. “You pay me back everyday just by being yourself.” She leaned over and kissed his cheek.   
They made it home and took off their jackets. Gwendolyn led Conan by the hand to the couch, encouraging him to sit. She pushed the coffee table out of the way and grabbed one of the throw pillows, placing it at his feet. Kneeling down on it, she smiled at him devilishly as she began unbuttoning his pants.  
“Oh, alright then,” Conan leaned back, relaxing.   
Gwendolyn shimmied his pants and boxers down part way and took his cock in hand, stroking it gently and rubbing her face against it, looking up at him. Making her tongue flat and wide, she licked up from the root to the tip before delicately encircling the head with her lips, sucking and flicking his slit with her tongue. Using her left hand to cradle his balls, her right hand made a tight circle around his base and swirled up and down as her head bobbed, swallowing him and sucking in time with the movements of her arm. His fingers found their way into her hair and his head fell back as his hips tipped forward, shoving himself deeper into her wet, eager mouth. She tugged gently on his balls, rolling them between her fingers and pulling her mouth off his cock for a moment to suck on them while stroking his shaft quickly with her hand. Returning her mouth to his cock, she took him deeper, hollowing her cheeks and pressing her tongue pointedly against the underside of his shaft. Rocking into her with enthusiasm, she could tell he was growing close as precum began to trickle in her throat, and she quickened her actions. Conan moaned gratefully, and Gwendolyn pressed her thumb to the space just behind his balls, pulsing gently, causing him to yell out her name as he came, hips lifting from the couch as he arched into her throat, hands pushing her fully down on his cock and burrowing himself deep in her throat.  
Conan fell back and Gwendolyn pulled off, wiping her streaming eyes. Breathing hard, he laid a hand against his rapidly beating heart.  
“Damn, that was a good one,” he said, reaching down to put himself away and do up his jeans.  
Gwendolyn sat next to him and leaned on his shoulder. He lifted his arm and put it around her. “Yeah. I love it when you lose control like that. It’s so hot,” she said. “I wish I had a recording of the sounds you make so I could use it when I masturbate.”  
Conan looked at her, taken aback. “You masturbate?”  
“Well, yeah,” she laughed. “I mean, pretty rarely now that we’re living together, since we’re having sex everyday anyway, but before we moved in together, on days we couldn’t get together, sure.”  
Conan smiled curiously. “What kind of things do you masturbate to?”  
“Oh, all sorts of things,” she shrugged. “Sometimes I use my imagination. Sometimes porn. I like videos of blowjobs.”  
Conan laughed. “Really?”  
“What can I say?” She held out her hands. “It just makes me really hot.”  
Conan placed his hand on her thigh, tracing invisible designs. “Would you ever consider…letting me watch you?”  
“Watch me…masturbating?”  
“Yeah…” he said softly. “I’ve never seen that in real life and I think it would be really sexy.”  
Gwendolyn tilted her head and lifted a shoulder. “Sure, I guess so. I don’t know if I’ll be able to, you know, cum though,” she said, blinking. “It might be kind of difficult with someone watching. But I’m willing to try.”  
Conan nodded. “Fair enough.”   
He kissed her on the forehead and they sat holding one another for a moment.  
“So…you want to go now?” Gwendolyn said.  
“Yeah?”  
“Yeah,” she stood up, heading to the bedroom.  
Conan followed her and cleared off the chair in the corner of their room. Gwendolyn undressed, pulling off her clothes and running her hands through her hair. She lay back on the bed and took a few long, deep breaths. Conan decided to take off his jeans and get comfortable now so he wouldn’t disturb her later. As he sat in the chair in his boxers in the twilit room, looking at her naked, splayed form breathing slowly, he already felt as if he were intruding on something private and it excited him. Without warning she brought her hands to her abdomen, running them up her body to cup her breasts, massaging them gently for a moment before circling back down, tickling her thighs idly then trailing her fingers over her mound, letting just the tips glide over herself. Taking her right hand and placing it between her legs, she painted back and forth with three fingers, not parting her lips but trailing over the sensitive skin, before applying soft pressure through the skin covering her clitoris. Then, using just her middle finger, she parted herself, stroking upwards with aching slowness, gathering wetness from below and spreading it to all areas of her sex. Inserting a second finger she began to circle her clit, not touching it directly, but her hips began to swivel in time with her movements.  
Conan was transfixed. Her movements were so careful, so precise. Her mouth parted as her breath quickened and he saw a pink flush beginning to creep along her flesh. Growing hard again in his boxers, he resisted the urge to touch himself, intent on her actions. Gwendolyn sped up now, applying pressure directly to her clit with every third or fourth rotation, chest rising fast as her wrist moved between her thighs. Soon she began using her middle and ring finger to apply direct pressure to her clit, rubbing hard up and down, heels digging into the bed as her free hand bunched into the comforter.  
“ _Fuck! Conan! Fuck, fuck_ ,” she gasped, catching Conan by surprise and he couldn’t help himself, he rubbed the head of his cock through his boxers as she thrashed and shook, her hand moving incredibly fast between her legs as she moaned, flailing and rocking back and forth with her eyes rolled back in her head, legs shaking uncontrollably as the last pulses of her orgasms tore through her.   
She held her hand stationary between her legs as she came down, catching her breath. After a minute or two she withdrew and her eyes fluttered open. Lifting herself to her elbows she looked at Conan. He stared at her with an expression that was simply ravenous.   
“Wow,” he breathed through his mouth, tongue flicking over his lips.   
Gwendolyn noticed his hard cock and the circular wet spot already staining his boxers. They gazed at one another for a moment, breathing.  
“Come here and _fuck me.”_  
Conan pounced in one fluid motion, not bothering to take off his boxers, just pulling out his cock and sliding it inside of her. Clenching his hands into fists to keep from coming immediately, Conan withdrew slowly before hammering home, pounding again and again as she writhed and groaned beneath him. One hand at her neck and the other gripping her arm, Conan dug into her, desperately holding on as he slammed into her, surprised at his own abandon. Shaking and thrashing, Gwendolyn came first, yelling “Fuck, Conan, _FUCK_!” And her nails grazed his back, but he didn’t notice the pain as she tightened around his cock and he fell apart, grunting and collapsing on top of her, submitting to his passion. Exhausted, they barely had the energy to crawl under the covers before sliding off to sleep.  
Alarm blaring, Conan reached over to slap it off and sat up in bed, rubbing his face.  
“Oh my god, Jesus,” Gwendolyn said when she rolled over.  
“What?” Conan turned around.  
“Your back!” She pointed. “I scratched the hell out of you! Go look!”  
Conan tried to look over his shoulder, but obviously couldn’t see, so he went to the bathroom to look in the mirror.  
“Holy shit,” he murmured. There were seven or eight gashes from her fingernails along his back.  
“There’s blood on the sheets!” Gwendolyn called from the bedroom. She followed him into the bathroom, putting her hair into a messy bun on top of her head.  
“Oh shit, look at you!” He said, pointing at her.  
“What?” She wiped a hand across her face.  
“Your neck! And look! Your arm! You’re covered in bruises!”  
Gwendolyn looked in the mirror, turning and peering at herself. “Holy shit, wow.”  
“Oh no…” Conan groaned, feeling sick. “People are going to think I beat you.”  
Gwendolyn shook her head. “Don’t worry. I can cover it with makeup and a scarf until it goes away,” she said, pressing on a particularly blue one high on her neck. “What about you though? What if you have to take your shirt off for a sketch or something?”  
Conan shrugged. “I’ll just have to talk my way out of it. They don’t come up too often, thankfully.”  
Gwendolyn nodded, turning to him. “Well, at least we had fun though, right?” She put her arms around his neck.   
“Definitely,” Conan kissed her. “Though maybe we should try to keep visible injuries to a minimum from now on.”  
Gwendolyn laughed. “Deal.”  
“Oh, hey,” Conan asked. “I’m curious, what exactly were you thinking about?”  
“Hmm?” Gwendolyn murmured as she applied toothpaste to her toothbrush.  
“When you were, you know…touching yourself. What did you think about?”  
Gwendolyn smiled at him in the mirror. “Well,” she began. “One of my go-to fantasies is that I go down on you in the back of a moving cab.” Conan raised his eyebrows and gave a little smirk. “I realize it’s impractical and couldn’t happen, you being such a recognizable figure and all, but I just love the idea of you trying to block the driver’s view somehow while I’m sucking your cock and you do your best to maintain a straight face.”  
She gave him a leering side glance that made him tingle, but even he had to admit he was running far too late already, so he simply chuckled and began brushing his teeth.  
—


	6. VI

That April, Conan was sitting on the couch, absorbed in a new biography of Mark Twain when Gwendolyn came to stand next to the couch.  
“So I went to an advanced yoga class today,” she said.  
“Mmhmm…” Conan didn’t look up.  
“And I got a deep tissue massage.”   
“That’s nice,” he murmured, turning the page.  
“And I did a few other things to prepare.”  
“Mmhmm…” still engrossed in his book.   
“And I asked around and found out this is the very best lubricant…”  
That broke through. Conan tipped the book down and looked at her over the top of his glasses. “What was that now?”  
She held out a hand. “Now don’t get too excited,” she said. “Because we’re going to have to go very slowly and we might not get far tonight.”  
Conan blinked rapidly. “Are you saying what I think you’re saying?”  
Gwendolyn smiled, nodding. “Well, it is almost your birthday…and you were so sweet with the NPH thing…I figured we could give it a shot.”  
Conan licked his lips. “So…now?”   
She shrugged. “Unless you’d rather finish that chapter you’re reading…”  
Conan threw the book over his shoulder, springing up as it clattered to the ground and following Gwendolyn to the bedroom. She’d set up the space ahead of time, putting a towel on the bedside stand with lube, baby wipes, a set of rubber gloves, and a small vibrator.  
“Okay,” Gwendolyn said, placing a hand gently on Conan’s chest. “Like I said. Slowly. I’ve done some research on anal so we’re going to have to work together and communicate, okay?”  
“Okay.”  
“And if I say stop, it absolutely means stop, okay?”   
“Of course,” Conan nodded.  
“Alright.”  
They got undressed. “It helps if the receiving partner is relaxed and aroused,” Gwendolyn said. Conan nodded and they began kissing. He ran his hands over her, massaging her scalp, rubbing her shoulders, and caressing her body. His fingers rubbing between her legs, getting her wet and excited, teasing her clit until she steadied his wrist.   
“Okay, okay,” she panted, and he pulled away. “Now from what I read it’ll be best if you start with your fingers, rubbing and stimulating at first before going inside. Use the lube, probably more than you think you need.”  
Conan nodded, his cock already hard and pressing against his thigh. Gwendolyn turned around, balancing on her knees and arching her back, lifting her ass into the air.   
Conan pulled back and she heard him popping open the lid on the lube.   
“Whether you use a glove or not is up to you,” she said. “But make sure if you don’t, you use a different hand on my vagina later. No cross contamination.”  
“Ah, okay,” Conan said, and she heard the snap of a glove over his wrist. Conan applied the lube to his index finger and began softly rubbing her, starting wide and working toward the center, applying more lube as he went. Once he felt her muscle begin to yield he eased the tip of his finger inside, twirling it around ever-so-lightly, creating a slightly wider opening. He slid up to the second knuckle, repeating the same patient process, noticing his mouth filling with saliva at the sensation of intense pressure around this single digit.   
Sliding his finger as far as it would go, he rolled it around inside of her. “You doing alright?”  
“So far, so good,” she said. Her breath was slow, controlled. He could tell she was counting it off in her head as he knew she often did when anxious.  
“Should I try a second finger?” He asked.  
“Yeah,” she said. “I’m ready.”  
Delicately Conan slid a second finger in along the first one. Then he began swirling them side to side.  
“Open and close your fingers slowly, like a pair of scissors, to gradually stretch it out,” Gwendolyn suggested.  
Conan did so, adding more lube, moving carefully and allowing Gwendolyn’s muscles to acclimate to his touch.  
“Okay,” Gwendolyn breathed after a few minutes. “Let’s try the vibrator.”  
“Okay,” Conan withdrew his fingers slowly and picked up the thin, silver instrument. “Um, I don’t know how to turn it on.”   
“Twist the base.”  
He did so and it sprang to life in his hands, startling him and he almost dropped it.  
“Make sure you apply lube to me and to it,” Gwendolyn said.   
Conan did so and began circling her opening, using the vibrations to relax her muscles before positioning the tip at her opening and sliding it in a little. Gwendolyn exhaled loudly.  
“Are you okay?” Conan asked.  
“Y-yeah, it just feels very…weird,” she said.  
“Is more okay?”   
“Will you…will you rub my clit a little first?” She asked.  
Reaching forward between her legs with his free hand, Conan began teasing and pressing her clit, rotating his fingers around and feeling her grow wet. She began pushing back against the vibrator, taking it deeper inside of herself. Taking her lead, Conan began gently rolling it side to side, opening her wider, all the while fingering her faster.  
“Okay, stop.”  
Conan froze. “Do you want me to take it out?”   
“No, no, I just don’t want to cum yet. You can keep moving the vibrator, just stop your other hand.”  
Conan obliged, gently pulsing the vibrator inside of her for about fifteen minutes, widening her gently with each rotation, all while resisting the urge to stroke his now-purple cock throbbing insistently against his abdomen.  
“Okay, I think I’m ready…” she breathed.  
“Yeah?”  
“Yeah. Make sure you use a condom. And a lot of lube. And go very, _very_ slowly.”  
“Of course,” Conan said, his shaking, high voice betraying his excitement. He unwrapped the condom and applied it to his turgid cock, slathering himself with lubricant. Applying a further dollop to her opening, he positioned himself behind her.  
“Ready?” He asked.  
She took a deep breath and let it out slowly, intentionally. “Yes.”  
Rubbing the head of his cock up and down against her opening a few times, Conan held himself firm and gently began to press forward. Gwendolyn gasped and he held still.  
“Stop?”  
She took a few deep breaths, unclenching her hands from the blankets. “I’m okay, it’s okay. Keep going. Just…slow.”   
Going a little further, she let out one high-pitched note before settling into labored breathing. “I’m okay, I’m okay,” she said. “Just give me a second.”   
Conan held as still as possible and it was excruciating. The head of his cock was half inside and the pressure was mesmerizing, but the last thing he wanted to do was hurt her, so he restrained himself.  
“Okay,” she said once her breathing returned to normal. Conan pressed forward a little more and the head of his cock slid inside, delicious pressure compressing him from all sides. He groaned at the same time Gwendolyn gave a muffled shriek.   
“How…How far are we?” She gasped.  
Conan swallowed. “The tip is in.”  
“Good,” she said. “Apparently that’s the hardest part. Just..Just hold still for a minute.”  
Conan did so, but it was brutal. Though compared to what Gwendolyn was enduring he had no complaints. He hungered for friction, but remained patient.  
“Do you want me to touch you?” He asked.  
“Yeah, yeah, that might help,” Gwendolyn said, breath labored.   
Conan reached down between her legs awkwardly, trying to stimulate her while also being careful not to move his hips forward. As he played with her, he noticed a slight loosening of the pressure around the tip of his cock, and soon Gwendolyn was moving against his hand, causing her to take him slightly deeper into herself. The combination of intense pressure and gentle friction was exquisite, and little moans grew in his chest as her body tugged on him with this novel pleasure.  
She started the slightest of moans and he couldn’t help it anymore.  
“ _Can I go in further?_ ” He knew he sounded like he was begging, and he practically was, but he didn’t care. He wanted it badly.   
“Okay, not too far too fast though, okay?” She panted.   
“Yeah,” Conan said, tilting his hips forward and sliding in another inch, hissing in pleasure at the pressure he’d yearned for before slowly pulling back and pressing in again. When he pulled back a second time he applied more lube before sliding back in, increasing his pace slightly both with his hand and his hips. As much as he wanted to push in all the way to the hilt he resisted the urge, only thrusting about half of himself inside. Gwendolyn ground herself into his hand, coming around his twiddling fingers and panting hard into the pillow. Conan backed off a bit, but kept his fingers on her, working her back into a second frenzy while his motions sped up above her. Growing close, he carefully thrust himself inside of her, placing one hand on her back to help him hold his distance. With three more thrusts he finished, leaning back so as not to push himself too far forward, shuddering with the force of his orgasm.  
Conan withdrew slowly and got up to throw away the condom. When he got back Gwendolyn was laying on her side and he joined her on the bed, reaching across to run his fingers through her hair.  
“You okay?” He asked.  
“Yeah,” she nodded. “It wasn’t easy, but it wasn’t as bad as I thought it would be, either.”  
“Well, thank you,” Conan said. “I know you did that for me and I really appreciate it.”  
She smiled, kissing the palm of his hand before getting out of bed and cleaning up. Coming back to bed in pajamas she crawled in, joining him under the covers, and as they lay there in the darkness they were both grateful for the trust they had in one another.  
——-  
A week later was Conan’s birthday, and as soon as he left for the office Gwendolyn set about baking a cake: vanilla with chocolate frosting, as requested. She found baking from scratch soothing, and particularly enjoyed dancing around the kitchen as she did so. Pulling the sponges from the oven to cool, she went to her closet to rifle through her lingerie for later, selecting a black, strappy negligee and tucking it somewhere easily accessible. After whipping up a chocolate buttercream and covering the cake, she made a darker chocolate icing and carefully wrote out “HAPPY BIRTHDAY CONAN!” On top of the cake, stepping back to admire her handiwork.   
Gwendolyn started dinner. Conan requested steak, and she made twice-baked potatoes and roasted Brussels sprouts to go alongside. Finishing up and setting the meat aside to rest, tenting it with aluminum foil, she looked at the clock. Conan should be walking in within the next half hour. Perfect.   
She went back to their bedroom and shimmied into the black negligee, hiding it beneath a tiny tight red dress that emphasized her bust. She finished her hair and makeup just in time to hear his key jingling in the lock, grabbing a small wrapped gift from the closet on her way to the living room.  
“Happy birthday!” She called as he opened the door, rushing forward to give him a kiss.  
“Aw, thank you,” he said. “It smells delicious in here.”  
“Sit down,” she gestured to the table, bringing over the food. They tucked into their meal, Conan expressing his thanks and delight, and when they finished Gwendolyn cleared the plates.  
“So, cake first or present first?”  
Conan considered for a moment. “Present,” he nodded.   
“Okay,” she handed him a long, flat package, holding a piece of paper behind her back.  
Unwrapping it hastily, he revealed a jewelry box. Opening it he exposed four sets of old-fashioned gold cuff links.  
He looked up at her, his expression a bit confused. She knew he only wore cuff links on special occasions.  
“Here,” she said, handing him the paper behind her back. “This might clear things up.”  
It was a certificate of authenticity from Sotheby’s indicating that they had once belonged to Dwight D. Eisenhower.  
“Oh wow,” Conan said, trailing his fingers over them. “Thank you so much.”  
“You’re welcome,” she kissed the top of his head and rubbed his shoulders. Turning around to get them each a piece of cake, she joined him at the table and they enjoyed the decadence. After, she cleaned up the kitchen and told Conan to go wait on the couch.  
“So I have another little surprise,” she said. “It occurred to me that you’re probably the type of guy who’s never really been to a strip club.”  
Conan chuckled lightly. “Correct. I mean, only as a joke for the show.”  
“Well, I thought maybe…if you wanted,” she stood up. “I’d dance for you.”  
Conan nodded. “Oh yeah. Definitely.”  
“Okay, well I’m going to get the living room ready,” Gwendolyn said. “I recommend changing into sweat pants, because, well…”  
Conan laughed. “Alright,” and he disappeared to their bedroom for a minute while Gwendolyn moved the coffee table out of the way and adjusted the lighting, making sure the stereo was cued up. Conan came back in his Red Sox pajama pants and sat on the couch, rubbing his hands together in anticipation.   
“Ready?” She asked. He nodded and she pressed play. A sensual song began and she whipped her hair forward, slowly drawing herself up and running her fingers through it as she twisted her hips from side to side. Reaching behind herself she inched down the zipper of her dress, turning around and showing Conan her back as she tipped each sleeve off before allowing the fabric to slither to the floor, kicking it aside. She turned around and dropped forward to the floor on her knees, laying back flat and running her hands over her breasts. Leaning back and lifting her legs into the air, she spread them in a wide V, gradually tipping them from one side to the other. Folding them underneath herself she came to her hands and knees and crawled toward him, running her hands up his shins to his knees, rubbing her cheek against the inside of his thigh. Standing up and turning around, she sat back in his lap, grinding her ass into his cock and draping her body across his chest. Conan brought his hands to her waist and instantly she turned around and placed them on the back of the couch.   
“Look, don’t touch,” she whispered, wagging a finger in front of him.  
He gave her a half smile, running his tongue over his teeth and nodding.  
Gently she removed the outer gauzy layer of her negligee, running it between her thighs before tossing it to the floor. Swaying back and forth as she went, she turned around and reached behind her to undo the clasp of her bra, looking at the hungry expression in Conan’s eyes over her shoulder as she removed the straps. Turning around and covering herself with one arm she approached him, revealing herself and using her bra to hook behind his head, drawing his face between her breasts for a moment before tossing the bra away.   
Straddling him, she ground herself into his hard cock for a moment before leaning back and balancing her hands on his knees and lifting her legs in the air, twirling them luridly. Lowering them and standing again, she turned around and hooked her thumbs under the waistband of her thong, slowly inching it down as she bent over and stepped out of it. Lowering herself to her knees once again, she ran her hands up Conan’s legs, caressing slowly, lightly grazing the outline of his cock with her fingertips before proceeding up his chest. Leaning forward to kiss the inside of his thighs she proceeded upward, reaching his cock and placing her mouth over it, sucking on the tip through the fabric for a moment before climbing on top of him. Eyes heavy and hands gripping the back of the couch, Conan was breathing open mouthed as she looked down at him and began to grind, undulating her hips with slow, sure movements, his cock notched between the lips of her sex. Moving faster, the friction of the ever-moistening fabric between them achingly tantalizing as they rocked together, Conan pressing himself into her, frantically trying to hold back his hands as hers danced over his scalp, his arms, his chest. Leaning forward, Gwendolyn moaned in his ear, “ _Fuck, yes, yes,”_ and her back arched as her hips thrashed wildly. The friction became too much for Conan and he couldn’t help but grasp her in his final moments, holding her tight and thrusting hard, a hot, wet spot growing on his pants.  
After her quivering ceased, Gwendolyn rolled off of him and sprawled naked on the couch, breathing hard.  
“Wow, I haven’t had that much fun dry humping since…” Conan said. “Actually I don’t think I’ve ever had that much fun dry humping.” They both laughed.   
“Yeah, glad you liked it,” Gwendolyn said. “Happy birthday, love.” She leaned over to give him a kiss. She stood and picked up her discarded clothing, and went to put on some pajamas. When they got into bed that night Conan lay awake for a long time, listening to her breathe. Sometimes, when she was dreaming, she would murmur half-intelligible things and he found it adorable. Tonight he heard “Fuh muh Beh…” and had to cover his mouth to prevent his giggles from waking her. Conan rolled over and closed his eyes, grateful for a truly lovely birthday.  
—-

_Panting. Grinding. Wet. She moaned and writhed, fingers gripping the eager, talented head between her thighs. But she looked down and something was off, wrong. The hair between her fingers was dark brown, not orange. Wasn’t it supposed to be orange? But it felt so good, she couldn’t stop. Pulling him to her face, she ached to have him inside her. “Fuck me, Bill,” she commanded. He thrust into her, and the last thing she heard before she woke up was the sound of her own scream._

Gwendolyn’s eyes flipped open and she was breathing rapidly. Conan’s arm was draped across her chest as he slumbered peacefully. She felt sick, but at the same time she couldn’t deny the slickness evident between her thighs. It was just a dream. You can’t control your dreams. She told herself, shaking the thoughts from her head. Conan began to stir, eyes fluttering open.  
“Hey…” he mumbled sleepily.  
“Good morning,” Gwendolyn replied.   
Conan rolled over to kiss her, pulling her close. Running his hands over her breasts, he massaged her gently and trailed a hand underneath her pajama bottoms.  
“Mmm…” he purred. “I love when you’re ready for me.”  
Gwendolyn was nauseated, grateful he couldn’t read her thoughts. She compensated by kissing him harder, pressing herself into his hand insistently and reaching down to grab his cock. Conan began trailing kisses down her abdomen, heading between her legs, but she pulled him back up.  
“No,” she whispered. “ _Just fuck me._ ”  
He gave her a questioning look but said nothing, positioning himself and entering her with a sharp intake of breath. Pulsing inside of her with sure, steady strokes, Gwendolyn locked her legs around him, drawing him in and rocking her hips into his. They kissed passionately, hands flying about each other’s bodies as their tempo increased. Panting and heaving, bodies rolling together, they sped toward their ecstasy, clinging to one another and gasping in desperation. As they reached the pinnacle, whispers of love crossed their lips, and they fell into each other, relieved.  
When they parted, Gwendolyn buried her face in Conan’s neck and the dream in the back of her mind, convincing herself it was nothing more than an aberration.  
—-

  
When the show wrapped for a break, the network threw a party to celebrate the ratings and nominations. They rented a huge hall and all those involved were invited, and Conan of course asked Gwendolyn to accompany him.   
They stood before the mirror at home getting ready, Conan brushing his hair and Gwendolyn applying a deep red lipstick. Conan was wearing a narrow cut black suit with a burgundy tie and Gwendolyn wore a little black dress with a flowy hemline since she hoped there’d be dancing.  
“Ready?” He asked.   
She did a quick once over and nodded, following him out of the apartment.   
When they arrived at the venue they spent a lot of time saying hello to people before they were able to get a couple of drinks and find a table of their own.   
“Oh hey, there’s Bill!” Conan said with a wave.  
Gwendolyn spun around. “What’s he doing here?” She hadn’t meant to sound alarmed and she hoped Conan hadn’t noticed.  
“Well, I ran into him last week and he seemed a little down or something,” Conan said as Bill was weaving his way toward them. ”So I asked if he had anything going on tonight and when he said no, I said he should come along.”  
“Hey, how are you two doing?” Bill said as he made it to them through the crowd.  
“Oh, pretty good,” Conan answered.  
Gwendolyn nodded. She didn’t know where to look. Music was starting up and people were hitting the dance floor.  
“How about you, Bill? How are you doing?” Conan asked.  
He shrugged. “Oh, you know, okay I guess,” he looked over his shoulder. “You two going to get out there?”  
Conan shook his head. “I’m sure this one will drag me out there,” he pointed a thumb over his shoulder at Gwendolyn. “She loves to dance.”  
“You do?” Bill asked, looking down at her, tilting his head in a way that made her skin break out in goosebumps.  
“Yeah,” Gwendolyn nodded, swallowing hard and avoiding his gaze. “But he’s not the easiest person to get out on the dance floor,” she leaned into Conan.  
“That’s because you look beautiful when you dance and I look like a pelican being attacked by a walrus.”  
Bill giggled and Gwendolyn took a sip of her drink.  
“How about you Bill?” Conan asked. “Are we going to see you out there?”  
Bill shrugged. “Maybe. I don’t mind dancing if the occasion calls for it.”  
“Well, tell you what,” Conan took a sip of his drink. “Why don’t you take Gwen here for a spin? Save me at least some of the embarrassment.”  
Gwendolyn almost choked on her drink. Bill stammered.  
“Oh, I don’t know…”  
“Ah, c’mon, what’s the big deal? One dance. You’ll have fun,” Conan said, pushing them together.  
Try as she might Gwendolyn couldn’t think of an excuse that wouldn’t sound suspicious, so she nodded and Bill escorted her to the dance floor.   
Putting her hands at his neck, his found her waist, and they began to move. Unsure where to look, her face felt hot and she could feel him looking at her.  
“So I guess you made up then?” Bill said as they swayed and twirled.  
Gwendolyn nodded. “Yeah, yeah, we worked it out.”  
“That’s…good,” he swallowed.  
“How about you? How are you doing?” She asked.  
“Oh, you know…” he said. “It gets a bit lonely sometimes, but I’m okay.”  
“Well, I have a lot of other friends I could set you up with,” Gwendolyn said as he spun her around. “What’s your type? Maybe I can do better this time.”  
“My type? Hmm…” he contemplated, replacing his hands at her waist. “”I dunno. Tall, curvy,”  
He pulled her a little closer with his fingertips. “Red hair.”  
Her eyes flicked upward and met his for the first time that night and saw what she feared most: yearning.   
“Bill…don’t…” she whispered.  
He shook his head almost imperceptibly. “I know, and…I-I’m sorry. But it’s been driving me crazy and I had to say something,” his thumbs rubbed small circles into her waist as they swayed back and forth.  
“Bill, you know that—“ she looked over at Conan.  
“I know, I know,” he stopped her. “I’m not expecting anything. I just had to say it. Just once. And maybe…maybe now it’ll go away.”  
Gwendolyn blinked and looked away, swallowing hard. “I hope for your sake it does,” she said as the song ended and they parted. She shook her head like an etch-a-sketch, replacing her expression with a benign smile and hoping Conan wasn’t secretly a lip reader as she walked back to him.  
“You looked like you were having fun,” he said as she made it back to their table. Gwendolyn nodded and forced a smile. “Just let me finish this drink and I promise I’ll take you out there,” Conan sipped his wine.  
They spent the rest of the evening talking, laughing, and dancing. All in all it was pleasant, but Gwendolyn couldn’t ignore the feeling of queasiness that rose in her throat, accompanied by an unnamed something buried, every time she pictured that longing look in Bill’s eyes.  
—-

  
Gwendolyn’s birthday was approaching and Conan found himself excited. He ordered her gift a month in advance and it arrived just in time. He waited for a night when she was out with friends to wrap it and hid it at the top of the closet where he knew she couldn’t reach without getting the foot stool.   
Conan asked her to meet him at Rockefeller Plaza that afternoon, a newspaper tucked under his arm. She met him in the lobby, smiling. “Hey, what’s up?”  
“Come on, let’s catch a cab,” he said.  
“Oh, a surprise?” She asked coyly.  
Conan just shrugged and gave a half smile. They stepped outside and soon a cab rolled up. Hopping in, he gave the driver an address in Brooklyn.  
“Brooklyn? What’s out there?” Gwendolyn asked softly, looking at him.   
Conan simply unfolded the newspaper, holding it in front of him. He looked at Gwendolyn meaningfully, then down at his lap.  
She tilted her head toward the driver as if to say _Really_? And Conan gave her the slightest nod. Gwendolyn let out a shuddering breath and began inching her hand over Conan’s thigh, reaching his fly and pulling it down as silently as possible, grateful that the driver was listening to loud salsa music. Reaching her hand into the depths of his jeans and past his boxers, she grasped his already thickening cock and pulled it free, starting to pump delicately. Waiting for a moment when the driver was focused on a particularly tricky left turn, she sank to her knees, wedging herself between the back and front seat as best she could and putting her head under Conan’s left arm. Taking him into her mouth and beginning to suck, she heard his fingers crinkle in the paper. Trying to move quickly and quietly, she used one hand to jerk him into her mouth as she sucked on the tip, whipping her tongue around and flicking the tip against his slit. She could feel the rise and fall of his chest speed up against the back of her head and he was clenching his teeth and breathing hard through his nose to avoid making a sound.  
“Some traffic, sir,” the driver said.  
“N-no problem,” Conan replied, his voice high and unusual. He began to ever-so-lightly tilt his hips forward into her mouth, crumpling the paper further and curling over her a little as he got close. Bobbing faster, Gwendolyn took the entirety of his length in her throat and he threw his head back, managing to turn a strangled sound into a clearing of his throat as he came in her mouth, quivering with each wave of his orgasm. Once he finished she pulled off, tenderly replacing him in his pants and zipping him back up before extricating herself and sitting up, smoothing down her hair.   
About ten minutes later they pulled up outside of a little deli. Conan paid, thanked the driver, and they got out.  
“Wow,” Gwendolyn exhaled dramatically. “That was…hot.” She rubbed her forehead.  
Conan tossed the newspaper in a nearby recycling bin. “Yeah, well, happy birthday,” he said, leaning in to kiss her. “Though it seems a bit selfish getting my dick sucked for your birthday,” he laughed. “I just thought, you know, since you mentioned it…”  
“No, no,” she shook her head, brushing back his hair. “It was perfect,” she lowered her voice to a whisper. “I am on _fire_ right now. I loved it.”  
Conan wrapped his arms around her. “Well, we don’t actually have to eat here,” he gestured toward the restaurant. “It’s a good place and all, but I just picked it so we would have a long cab ride.”  
Gwendolyn shrugged. “We have to eat. Might as well be here.”  
They went inside and ordered a couple of sandwiches and pickles and sat down at a little rickety table in the corner. The place was pretty crowded for a weekday and they had to weave their way through the other patrons.  
“You know what they say about pickle juice,” Gwendolyn said as Conan chomped down on his dill.  
He shook his head. “No, what?”  
“Apparently it makes your cum taste better. That and pineapple juice,” she took a bite of her sandwich.  
“Really?”  
She shrugged. “I have no idea if it’s true. Can’t say I’ve ever tested it.”  
Conan chewed for a minute. “Well…what does it taste like?”  
Gwendolyn stared at him. “You mean you’ve never tried it?”  
“No!” Conan pulled a face. “Of course not!”  
Gwendolyn pulled back her head. “I don’t know how you couldn’t be curious! That’s crazy! If it were me I’d have to try,” she took another bite, chewed, and swallowed. “Well, it’s kind of hard to describe I guess,” she thought for a moment. “Saltyish. And not everyone’s the same, diet makes a difference and stuff,” She took another bite before setting her sandwich down. “You know what is probably closest in flavor? Brie cheese.”  
“Huh,” Conan said. “Weird.”  
She shrugged. “I don’t mind it. Obviously. But I get why some people do.”  
They ate in silence for a few bites before Conan spoke. “Maybe I’ll get some pineapple juice and we can test it out,” he said, finishing his meal. “You know, drink two—three glasses a day, see if it actually makes a difference.”  
Gwendolyn shrugged. “Yeah, I’d be curious to find out.”  
They finished up and left the deli, catching a cab back to Manhattan. When they arrived home Conan asked Gwendolyn to sit on the couch. “Wait here, just a minute,” he said, disappearing into the bedroom. Reappearing around the corner with a small rectangular package in shimmery purple wrapping paper, he handed it to her, joining her on the couch.   
“Happy birthday,” he kissed her lightly.  
She smiled. “Thank you,” and began carefully unfolding the paper to reveal a book. Turning it over her eyes went wide.  
“Is this…is it…a first edition?”  
Conan nodded. Gwendolyn put her hand over her mouth in surprise before running her fingers lovingly over the gorgeous cover. It was John Steinbeck’s _East of Eden_ , one of her favorite novels and incredibly hard to find. She cradled it in her hands as though it were made of glass.  
“Oh wow, Conan, this is amazing. Thank you so much,” she took him by the back of the neck and kissed him warmly. “It’s really beautiful.”  
Conan rubbed her back. “I’m glad you like it.”  
She nodded, clutching it to her chest. “I love it.”  
“Okay, come on,” he said, pulling her to her feet and guiding her to the kitchen. He gestured her to a seat at the island and reached into the fridge, emerging with a small cake box. Taking out a small yellow cake he bedecked it with one candle and rifled through the drawers for a lighter. Kneeling next to her, he began to comically sing ‘Happy Birthday!,’ unnecessarily extending each syllable, causing Gwendolyn to laugh uproariously.  
“You should make a wish,” he said. She closed her eyes and blew out the candle. Conan pulled it free and cut them each a slice.  
“Lemon?” She asked.  
He nodded, licking frosting off his finger as he set a plate before her. “Your favorite, right?”  
“Yup,” she smiled, leaning across the counter to kiss a bit of frosting from the corner of his mouth.   
They finished their cake and Conan cleaned up, insisting that Gwendolyn was not allowed to help. He came around the kitchen island, turning her in her chair and placing his hands at her waist before leaning down to begin kissing her neck.  
“So,” he hummed into her flesh. “Bedroom?”  
She nodded against him, already standing to follow his lead. Undressing one another feverishly, Conan lay her naked onto the bed, following her and massaging her skin, trailing his hands with his lips, kissing every inch of her he could reach. Making his way between her thighs, he lightly brushed her lips with the tips of his fingers, pressing soft kisses to them before spreading her open. Starting in wide circles and working inward, he twirled his tongue around her clit, her hips rotating in time with his movements as her breath hitched. Sliding his fingers inside of her he began to coax her toward him, and soon she was grinding her pelvis into his face, moistening his chin as he began to suck on the hardening pearl of her sex. Fingers clenched in his orange hair, she breathily called his name, squirming against him, shuddering as his movements quickened. He felt her flutter and twitch around his fingers and the cascade of her orgasm rent through her trembling form, causing her to rock back and forth helplessly, a font of high-pitched expletives pouring from her lips.  
Conan emerged, kissing his way up her body, and pulled her upright. He sat back against the headboard and patted his thigh, encouraging Gwendolyn to climb on. Eagerly she abided, sinking down on his cock in one fluid motion and throwing back her head with a gentle groan. Holding on to the headboard for support, she raised and lowered herself intensely, slamming down hard and bouncing back with a swivel of her hips. Conan’s right hand worked between her legs to stimulate her in time with their movements and soon she was riding him wildly, hammering vigorously, the headboard violently shaking against the wall. Using his left hand to grip her hip, Conan lifted himself up to her, but he struggled to keep up with her voracious movements as her auburn hair swirled around him and the sounds of her ecstasy filled his ears. Eyes rolling and head thrown back, she came hard, hips dancing as her legs shook uncontrollably. She was breathing hard and pulsing against him, so Conan lifted her and lay her back on the bed, climbing on top of her and beginning to drive deep inside of her, drawing new depths of sound from within. As he neared orgasm and her hips swirled gently beneath him, he propelled himself forth as fast as his body would allow, releasing himself inside of her and yelling out her name before they collapsed into a sweaty, panting heap of limbs.  
Once recovered, they ordered some dinner for delivery so Gwendolyn wouldn’t have to cook, and spent the rest of the evening quietly enjoying one another’s company.  
“So, good birthday?” Conan asked as they climbed into bed.  
Gwendolyn nodded. “Perfect,” she leaned over to give him a kiss before turning off the light. “Thank you.” They curled up together under the blanket and as Gwendolyn drifted off in Conan’s arms she hoped her wish would come true, that she would spend every birthday to come by his side.


	7. VII

As August approached, Conan began to develop a plan, doing his best to hide it from Gwendolyn as he made arrangements from the office and returned phone calls while she was in the shower.  
When the day arrived Conan woke up early and knelt by the bed in front of Gwendolyn’s sleeping face.  
“Pack your bags, baby!” He yelled, scaring the hell out of her.  
“Wha—?” She shot up, rolling over and getting twisted in the covers, forcing her to slump down again.  
Conan fell over on the floor laughing as she disentangled herself.  
“Happy anniversary!” He yelled, jumping up and spreading his arms wide.  
Gwendolyn found his early morning enthusiasm daunting as she rubbed the sleep from her eyes.   
“Pack…what now?”  
“I’m taking you out of town! Come on, let’s go!”   
She processed this information slowly. “Where are we going?”  
“It’s a surprise,” he leaned down and kissed her forehead. “Just start packing and we’ll head out.”  
Gwendolyn nodded, yawned, and got up. After waking up for a few minutes she went in the closet and unearthed her suitcase. “How do I know what to pack?” She called out to him in the kitchen.  
“Just pack enough stuff for three days,” he responded.  
“Hot or cold weather?” She asked.

“Hot.”  
“Swimsuit?”  
“Yeah,” he called back. “Teeny bikini, preferably.”  
She chuckled and began combing through her closet, packing her bag and zipping it up, selecting an outfit for the day as well.  
She hauled it out to the living room. “Did you get sunscreen?”  
“SPF 1000,” he responded. “Check.”   
She nodded. “Is there time for breakfast?”  
“We’ll get it on the way!” He said, energy almost manic. “Come on!”   
He took her suitcase and they went downstairs, loading up the car. He opened the passenger door for her with a flourish before climbing behind the driver’s seat.  
“ROAAADDDD TRIPPPP!!!!” He yelled loudly, rolling down the windows and peeling out. Putting a CD in the drive, he began to sing along boldly and Gwendolyn giggled helplessly, charmed by his exuberance.   
They stopped at a small diner and got breakfast before hitting the road, and they spent their drive singing, talking, and laughing as the hot summer sun beat in through the windshield and a cool breeze blew in through the open windows, twisting their hair about their heads.  
About three hours later they turned off onto a bumpy, rocky side road that went for half a mile before revealing a quaint beach front log cabin.   
“Here we are,” Conan slid the car into park.   
Gwendolyn looked around in awe. “It’s perfect,” she said. There were woods on either side and not a neighbor in sight. Way far off across the lake she saw a lone boat puttering along, but that was the only sign of humanity.  
They climbed out of the car and grabbed their bags. Conan fished the key out of his pocket and they went in. “Oh, I almost forgot,” he went back to the car and hauled a huge cooler inside that must’ve been in the trunk. “Sustenance.”  
Gwendolyn was a little nervous about what Conan would deem “sustenance” since he didn’t know anything about cooking, but it was only three days, and as long as it would keep them alive, that was enough.  
The cabin was an adorable one bedroom. No television, but thankfully equipped with A/C. They brought their bags into the room and unpacked, and Conan unloaded the cooler, which turned out to have fresh fruit and vegetables, and pre-made meals of salads, sandwiches, and pastas from one of their favorite delis. Once everything was in its place they looked around appraisingly.  
“So, want to get in the water?” Conan asked.   
Gwendolyn nodded eagerly and found her swimsuit. As requested, she brought along a red string bikini and Conan slapped her ass appreciatively after she changed. She giggled and they grabbed a couple of towels and the sunscreen and made their way down to the beach. The sand was white and warm, and they laid out their towels a couple of feet from the water and began slathering their pasty skin with the sunscreen.   
“Will you get my back?” Conan asked. Gwendolyn obliged, running her hands over the myriad of freckles, making sure to get his neck and hairline and turning so he could do hers.   
“Hold on, you missed a spot,” he said.  
“Where?” She said, turning and looking herself over.  
“Right about _there_ ,” Conan said, smearing sunscreen on her breasts and pushing her bikini aside.  
“ _Conan_!” Gwendolyn said, frantically covering herself. “What if someone sees?!”   
“That’s the whole point of all this,” he leaned in, taking her by the waist. “There’s no one around to see us.” He kissed her deeply, reaching down and grabbing her ass shamelessly and dragging her toward him. He gave her a light spank and they separated, sitting on their towels for a few minutes to allow their sunscreen to set before going in the water.   
As they waded in it felt pleasantly cool, and they could clearly see their feet at the bottom even as they made it in past their waists. Conan lifted Gwendolyn, hooking one arm under her legs and cradling her in the other and swirled her around in the water. She held on to his neck, leaning her head peacefully on his shoulder. Setting her down, he began kissing her intensely, fingers playing with the hem of her bikini bottom before sliding underneath.  
“ _Conan_ …” she whispered.  
“Aw, come on,” he smiled against her mouth. “No one’s looking…” He slid his hand between her thighs, rubbing her gently and kissing her neck. She reached down and began to palm his cock through his bathing suit, tugging him for a few moments before sliding beneath the waistband and taking him firmly in hand. Growing wet between his fingers, Conan pushed the fabric of her swimsuit to the side and crouched down in the water. Positioning her over himself, he removed his cock from his bathing suit and lowered her. Gwendolyn gasped, little tendrils of her hair trailing in the water as she bounced up and down on his cock. They kissed feverishly, ripples emanating from where they rocked together, his hands tight on her hips to assist the friction as he thrust into her. Gwendolyn bit her lip to suppress a scream, bobbing fast as they came together, Conan letting out a keening moan, and they gripped one another tightly as the sound of lapping water caressed the beach.  
When they separated they floated idly for a while, enjoying the soothing rise and fall of the water. Deciding to swim out deeper, they were treading water and looking at the beach when Gwendolyn turned to Conan.  
“So, one year,” she said, whipping water out of her face.  
“Yup.”  
“How are you feeling about it?”  
“Great,” he said, holding himself up. “Lucky. You?”  
“Same,” she said. “And I don’t get so scared anymore.”  
“What do you mean?” He asked.  
“I dunno,” she spit out some water that had gotten in her mouth. “Scared of fucking it up, I guess.”  
Conan nodded. “Yeah, yeah, I know what you mean.”  
They smiled at each other as they struggled in the water, then decided to head back to shore. Walking onto the beach and flopping down on their towels, Conan immediately stood up.  
“Hold on,” he said. He toweled himself off a bit and ran inside the cabin, then came out holding what turned out to be a camera aloft.  
“Aw, none of that,” Gwendolyn shied away.  
“C’mon,” he said. “We have almost no pictures together.”  
She sighed. “Fine,” and she put one arm behind her head, the other one her hip, giving him one pin-up pose.  
“Mmm…sexy,” he said, peering at her through the camera lens.   
“Now come on,” Gwendolyn stood up and knelt down next to him. They kissed and he turned the camera around, snapping a photo of them halfway between kissing and smiling against one another.   
Not wanting to burn, they toweled off and went inside for lunch, which was a delicious cranberry chicken salad and fresh strawberries. They showered a took a nap, waking just as it was getting dark. Curling up and reading for a bit, Gwendolyn noticed Conan staring at the same page for a long time, but didn’t comment on it. Soon he was looking to the clock every few minutes, and though she was curious, she focused on her book. She got up to go to the bathroom and when she came out Conan was standing in the doorway.  
“Let’s go out to the dock and look at the stars.”  
Gwendolyn nodded and followed him, the wooden boards creaking underfoot as she made her way to the end of the dock. They leaned against the railing and looked up. Clear and crisp, it was the first time she’d been away from the light pollution of the city in a long time and it was breathtaking. The sheer volume of stars was dazzling.  
“Oh!” She exclaimed as she saw a meteor streak across the sky. It was followed by another. Then two more.   
“It’s the Perseids,” Conan whispered in her ear from behind, his arms around her waist. “One of the biggest meteor showers of the year. I wanted to take you all the way out here so we could watch it together.”   
She reached back and cupped his face, kissing him. “Thank you.” She watched the stars falling in awe and didn’t notice his hands leave her waist.  
“Gwendolyn…”  
“Hmm?” She was looking up, mesmerized. When she turned around Conan was down on one knee, holding out a small velvet box.   
Her breathing stopped, heart frozen, she stared down at him, his beautiful features etched in moonlight.  
“Gwen, I love you more than I believed possible, and I want to spend the rest of my life with you beside me. Gwendolyn Greene, will you marry me?”  
It was as if her brain was crashing. She could not compute the information before her. Finally, she willed herself to nod.   
“Y-yes, yes!” She choked out. Conan stood and swooped her into his arms, his lips meeting hers as tears streamed down her face. He pulled back and smiled, taking her shaking hand and sliding the ring on her finger. She kissed him again, somewhere between laughing and crying, holding him near as they swayed back and forth at the end of the dock, the heavens raining starlight all around.  
They parted, eyes wet, and meandered slowly back to the cabin. When they got inside Gwendolyn admired the ring in the light. It consisted of a silver band holding five stones that looked to be opals in a sporadic arrangement, making it look like a tiny constellation decorating her finger.  
“Oh, it’s _perfect_ ,” she cooed, twisting it back and forth to catch the light. “How did you know?”  
“Well,” Conan wrapped his arms around her from behind, resting his chin on her shoulder. “I snagged your phone one morning when you were in the shower a couple of months ago and found your friend Missy’s number and asked her for advice. She sent me some photos of rings she knew you liked and I brought them in to a jewelry designer a guy at work recommended, and this is what they came up with.”  
“A couple of months ago?” She turned in his arms to face him. “You knew all that time that you wanted to marry me?”  
“Gwen,” Conan pushed back a lock of her hair. “I’ve known since the first week we were together that I wanted to marry you…”  
Tearing up again, Gwendolyn lifted her lips to his and they sunk in to one another. Conan walked her backwards toward the bedroom, never breaking their embrace. Pulling their shirts over their heads they exposed their sun-warmed skin, Conan brushing kisses over her shoulders, her neck, nipping lightly at her earlobes. Gwendolyn ran her hands up his arms, rubbing his neck before gently grazing his chest with her fingernails. She reached back and undid her bra, tossing it aside, and he took her breasts in hand, his nimble fingers exciting her nipples and cupping her softly. Undoing his jeans and working them down his hips, Conan pulled them down the rest of the way along with his boxers, exposing his erection which Gwendolyn rubbed lovingly. Stepping out of her underwear, she lay back on the bed and Conan followed, pressing his lips to hers and massaging her hip and thigh. Inching his fingers between her legs, she was wet and ready as he spread her open, pulsing with two fingers against her engorged clitoris, causing her mouth to fall open underneath his own. Rubbing faster she ground herself into him, moaning and clutching on to him as her legs began to tremble. As the tremors erupted through her, she gasped his name, folding herself into him.   
Conan waited a moment for her to come down and brushed her hair away from her face, looking into her eyes.  
_“I love you,_ ” he whispered.  
_“I love you, Conan_ ,” Gwendolyn swallowed hard past the lump in her throat.   
Maintaining eye contact he entered her, and for a while they held still, finding solace in the closeness of their skin. When the rhythm of their lovemaking began, their bodies sped forth but their eyes held still, holding unspoken volumes and silent promises. Racing ahead, fingers and breath entwined, their bodies rolled and crashed, and as they stared ahead into the ill-defined darkness they strode forth, fearing nothing while at one another’s side.   
They clung to one another, aftershocks skipping through their bodies. Conan kissed Gwendolyn’s sweaty forehead before rolling off of her, and she smiled over at him, exhausted. They fell asleep on top of the covers, managing to crawl halfway under in the middle of the night. Gwendolyn found herself lying awake at around three a.m., the lapping of the lake and the sounds of the forest incredibly foreign compared to the noise of the city. She looked at Conan, sleeping peacefully, his features all blues and grays in the moonlight coming through the windows, and she had to resist the urge to touch him. Looking down at the ring sparkling on her finger she took a staggered breath as tears once more threatened her eyes. She attempted to sleep again, overwhelmed with her own blessings.  
The next morning Gwendolyn woke to Conan making breakfast. And by that, of course, she meant he was opening containers of food made by other people. Shuffling to the kitchen she joined him at the table and they shared a meal of fruit and bagels. After clearing up, Conan noticed her admiring the ring.  
“Well, are you ready to spread the news?” He asked, kissing the top of her head. She nodded and clapped enthusiastically.  
First they called his parents. His mother answered.  
“Hello?” Her voice came over the line.  
“Hey, mom.”  
“Oh, hello Pigeon Pie, how are you?”  
“Good, mom, good,” Conan said. “Is dad there with you? I’ve got some news.”  
“Sure, I’ll go get him.” They heard her muffled voice calling out and some scrambling noises before they both returned to the line.  
“Okay, we’re here. What is it, dear?”  
“Mom, dad, I’m engaged!” He exclaimed.  
“Oh, yay!” His mom said, his fathers voice garbled in the background. “To Gwendolyn?”  
Conan laughed. “Yes, mom. To Gwendolyn. I didn’t start seeing someone else in the last month and decide to marry her.”  
“Well, you know I was just checking,” she said, bristling a little.  
“I’m very excited to be marrying your son,” Gwendolyn said, leaning into the phone.  
“Aw, that’s sweet dear, welcome to the family!” His mom said.  
“Congratulations, son!” Piped up his dad. “Proud of you!”  
“Thanks, mom and dad.”  
“Now you two have a good time and be sure to let us know when the wedding is.”  
Conan chuckled. “We will. Have a good day.”  
“You too, love you.”  
“Love you, too. Bye.”  
Conan hung up and they repeated the process with his brothers and sisters, the conversations going much the same way. Gwendolyn called her best friend Missy, which consisted of a lot of screaming and jumping up and down, and a couple of other friends.  
After hanging up she joined Conan on the couch, admiring her ring again.  
“So…” he said. “Not to cast a pall or anything but…will your family really not be there when we get married?”  
Gwendolyn stiffened. “I have a couple of adopted cousins I’m on speaking terms with,” she said. “But beyond that, no.”  
Conan nodded. He knew she didn’t want his pity but the idea of her side of the hall being barren of relatives, having no one to walk her down the aisle, carved a sadness in him that was difficult to disguise.  
“So,” Gwendolyn said, changing the subject. “should we hit the water?”  
Conan nodded. They changed and went outside, liberally applying sunscreen once again to their pasty skin. Bringing books and towels they lay under the hot sun, reading together peaceably. They spent the rest of the day swimming, splashing, and cooling off inside, enjoying their own little bubble of solitude and making their way to the end of the dock to watch the sunset, hues of pink, orange, and purple dappling the surface of the lake as they held one another close.  
The next day they slept in, then took a quick dip before showering and packing up to leave. The ride home went by quickly, and as the buildings grew taller and closer together their time on the beach became a warm memory.   
——

A couple of weeks later they were having dinner and Conan was flipping through his planner.  
“So what do you think of April 11th?”  
“Hmm?” Gwendolyn chewed.  
“As a date,” Conan said. “You know, for the wedding.”  
“Oh!” Gwendolyn said, surprised. “Yeah, sure. I mean, I don’t see why not.”   
Conan nodded, circling it. But as Gwendolyn returned to her potatoes a pit began to form in her stomach.   
That night she slept restlessly, fighting her own mind. It was about three before she finally came to her decision. Apprehensive, but certain she was making the right choice, she steeled herself for the conversation to come.  
The next day when Conan got home from work they had dinner, and after he grabbed a glass of water and went to read on the couch. Joining him, Gwendolyn sat staring at her book, not absorbing a single word as she gathered her courage.  
“Conan, can I talk to you about something?”  
“Yeah, what’s up?” He asked.  
“It’s kind of important.”  
He put the book down. “Okay, I’m listening.”  
“So,” she began. “Now that we’re going to be married, I think it’s really important that we don’t have any secrets from each other.”  
Conan nodded.  
“So,” she swallowed, her mouth suddenly dry. “Do, um, do you remember when Bill and Laura broke up? And I brought him cookies?”  
“Yeah…” Conan said, narrowing his eyes slightly.  
“Well, I also brought him some bottles of wine. Which we drank while we talked about her and, um,” she took a deep breath, letting it out slowly. “We ended up kissing.”  
It was as if someone flicked a light switch off behind his eyes. Cold and dark, he stared back at her, unmoving for a full minute.  
“Conan,” she whispered. “Please…say something.”  
He turned away from her and looked at the floor, clearing his throat. “W-who kissed who?”  
“He kissed me,” she stated. “But I-I didn’t stop him right away.”  
Conan held himself frighteningly still. “What I don’t understand is…” he said softly. “Is this was _months_ ago,” he shook his head, not looking at her. “And what, you were just never going to tell me?”  
“I was afraid…” Gwendolyn hung her head.  
“Afraid of what?” He asked flatly.  
“Afraid you would leave me…” she whispered.  
“Well, you were fucking _RIGHT_!” He exploded, standing up and grabbing the glass from the table, hurling it against the wall where it shattered. He rounded on her, fiery eyed and red faced.  
“ _Conan, Conan, please…_ ” she begged, but his hands were balled into fists at his sides and he was shaking with rage.  
“HOW THE HELL AM I SUPPOSED TO TRUST YOU NOW, GWEN?” He screamed, throwing up his hands. “HOW?!”  
“Please, Conan, _please_ , I’m sorry…” she sobbed.  
But he just held up a shaking hand, turning half away from her.   
“Give me the ring,” his voice was flat, dead, empty.  
“No, please, Conan, _don’t_ …” she begged, clutching her left hand to her chest. “Don’t throw away what we have together.”  
He rounded on her, getting close to her face, voice deadly. “I didn’t throw anything away, Gwen. _You_ did this. You.” He backed off and looked away from her, holding out his hand. “The ring.”   
She held it forth in a shaking hand and he snatched it from her.  
“Now get out,” he said, monotone voice barely above a whisper.  
“ _Conan, please_ …” she sobbed.  
“I said GET OUT!” He screamed.   
Eyes blurred with tears she grabbed her purse and shoes and went to the door. She looked back and Conan was facing the wall, not looking at her. Weeping, she shut the door behind her, walking out onto the lonely New York streets.  
——

  
Gwendolyn found a mid-range hotel and checked in.   
“One night?” The front desk clerk asked.  
That question alone almost pushed her to tears again. “Can I, um, start with one with the option of staying longer?”  
The clerk nodded. “No problem.”   
Gwendolyn went up to the room and looked around at its pristine, impersonal décor and flung herself forward on the bed, wrapping her arms around a pillow, body wracked with sobs. She didn’t know how long she cried, but when she was reduced to a chilled, sniffling puddle she drew herself up, undressed, and ran a hot bath with the tiny hotel body wash, making the water as hot as she could stand. She wanted it to hurt, to sting, hoping she could sweat out some of her grief.   
Ordering room service, making sure to get a few drinks as well, she noticed the time and against her better judgment turned on the tv. There, smiling down at her with his signature orange hair and crisp suit was her beloved, Conan. For the first time she did not laugh at her funny man whom she loved so dearly. She wept, rocking herself back and forth, seeing him perform through a curtain of tears and aching to look over and see him in the bed next to her.  
She slept poorly and when she awoke the next morning she decided to risk sending Conan a text.   
“Can we talk?”  
Anxiously she awaited a reply but none came. By the second day in the hotel she had to admit she needed a few things, so she waited for a time when she knew he would be at work and snuck back to the apartment, gathering some clothes, toiletries, and her computer. Looking around at the home they shared, she felt her chest constrict, desperate to stay in the first place where she felt she belonged in her life.  
Every night in the silent hotel room she turned on his show. She knew it was stupid, that she was picking at the scab and it wouldn’t heal, but she couldn’t help herself. Gwendolyn liked to think that she saw a sadness behind his eyes in those quiet moments between jokes, but maybe that was wishful thinking. Maybe one of the parade of gorgeous actresses that graced his stage had already taken her place in their bed. Maybe she was already forgotten.   
Her eyes stung and she hugged herself. She decided to take another chance and texted him again, just three words.  
“ _Please, my love.”_  
——  


As Conan heard the door click shut behind her he felt tears, hot and wet spill onto his cheeks and he resented them. He didn’t want to cry for her, didn’t want to be sad. He wanted to rage and scream. He wanted to go into her office and punch holes through her paintings, tear her books in half. He settled for sitting on the couch and screaming into one of the throw pillows, but he was betrayed by his body, and as the screams turned to sobs, he folded in half and rocked helplessly.  
When he finally calmed he cleaned up the broken glass, then dragged himself to the bedroom and flopped down on the covers. Taking one deep breath he recoiled. _Gwendolyn_. Her smell permeated the pillows, the blankets, the sheets. Unplugging the alarm clock and taking it with him to the guest room, he laid on top of the blankets, not bothering to get undressed and falling into a fitful sleep.  
Conan got her text the next day and ground his teeth, ignoring it. He did his best to go about his business at work, but he could hear himself biting people’s heads off, watched himself being a jerk, but seemed helpless to stop it. He spent half his day apologizing to people and finally Andy came into his office and closed the door behind him.  
“Alright, what’s going on?” He took a seat across from him.  
“I don’t know what you mean,” Conan pretended to shuffle papers on his desk to avoid eye contact.  
“Don’t give me that, man. Something’s up. I’m just going to say it: you’ve been a real dick all day.”  
Conan looked up, his first instinct to flare up, but he took a breath and deflated. “Yeah, okay…” he hung his head. “Um…” he looked at the ceiling, blinking. “Gwendolyn and I got in a fight and, uh…” he swallowed. “I think things are…done.”  
Andy sat open mouthed. “Oh no, really?”   
Conan nodded, fighting hard not to cry in front of his friend.   
“Well,” Andy said carefully. “Obviously I don’t know what happened, and you can tell me to go to hell, but…” he tapped the arm of the chair. “You two? That kind of love? You don’t see that everyday. So if there’s a way to fix it, I hope you find it.”  
“Thanks, Andy,” Conan nodded, sniffing a little. “And I’ll try to take it easier on everyone.”  
“That’d be good,” he said. “Let me know if there’s anything I can do to help.”  
Conan nodded and Andy stood to leave.  
All week Conan stayed as late as he could. Making small talk, volunteering to do small, odd jobs. Being in the apartment was painful. Every surface had her touch. Even asleep he couldn’t escape her. Visions of swirling auburn hair and green smiling eyes came to him and he would find himself waking up with one arm extended, only to find an empty half of the bed beside him.  
He noticed she must’ve come home one day to grab some things. He wondered where she was staying. _I bet she’s with Bill._ An evil, taunting voice in the back of his head suggested. Clenching his fist so hard his nails left half moon dents in his palm, he pushed that thought away, doing everything possible to distract himself from the thought of them together.  
After a week he unbuckled his briefcase at work and took out a book. He had a few extra minutes before his next meeting and wanted to get into this new biography. Opening the cover, something slid out and fluttered to the floor. Conan reached down to pick it up and flipped it over. It was the photograph of Gwendolyn taken at the beach, when she’d gone into a pin-up pose for him. Body glistening in the sunshine, she smiled widely at him through the picture. They were so happy. He turned the photo over and saw that she scrawled him a note.  
_“A little piece of cheesecake to get you through the day. Love you forever. Xoxo. Gwennie.”_  
Conan smiled in spite of himself. He didn’t even know she’d had prints made of those photos, much less that she’d snuck this one into his book. Just then the phone rang. He tucked the photo back into the book, closed it, and answered.  
——

After a week in the hotel and no answer to her texts, Gwendolyn wondered how much longer she should go before she faced the fact that she needed to look for a new place to live. The thought made her nauseous. She remembered how exciting it had been when she and Conan looked for their apartment together, the thrill of merging their lives and the anticipation of finding out about each other’s little quirks and habits. Now this.  
Turning to the blank page of her laptop, she sighed. Creativity eluded her and she stared as the blinking cursor mocked her. Then her phone buzzed.  
“Mortimer’s Deli. Tomorrow. 10 a.m.”  
It was from Conan. Her heart hammered in her chest. There was no indication of his mood, but the relief at being able to see him again was enough.  
“I’ll be there,” she sent back.  
Doing her best to doll herself up with her limited supplies and wardrobe, Gwendolyn set out for the deli, arriving at 9:50. Conan was already there, seated at a table in the far corner. The place was sparsely populated and he was stirring a cup of tea. Sliding into the seat across from him, Gwendolyn hid her fidgeting hands under the table.  
“Thank you for seeing me,” she said.  
He gave an almost imperceptible nod. They sat silently for a couple of minutes.  
Gwendolyn decided to take the plunge. “Conan, I’m so sorry, plea—“  
He held up a hand to stop her. She froze. “I have a few questions,” he said, not looking up from his tea.  
“Okay.”  
“First, is there anything else?” He asked. “Anything else I don’t know?”  
Gwendolyn took a breath. “The night we fought about…about my number, I went out and got drunk. And I spent the night at Bill’s,” Conan’s nose flared and his fingers gripped his cup. “But nothing happened!” Gwendolyn said hastily. “He just took me there to sleep because I was too drunk to find my way to a hotel.”  
“Nothing happened?” Conan still didn’t look at her.  
“We hugged goodbye.”  
“That’s all?”  
“That’s all.”  
Conan nodded. “Anything else?”  
“Well, the night of the wrap party, when you asked us to dance together.”  
Conan slammed his fist against the table, rocking his cup and startling a couple of nearby patrons before bringing his trembling fingers to his temple. “Yeah?” He asked.  
“B-bill told me he had feelings for me,” Gwendolyn swallowed nervously.  
“And what did you do?” Conan asked. She could see him shaking.  
“I told him I hoped he would get over it.”  
“So you don’t have feelings for him?” He asked.  
“No.”  
“Nothing?”  
Gwendolyn paused. “I would be lying to you if I said I didn’t think he was a good looking man, but no, I do not have any emotional feelings for him, nothing I’d ever want to act on.”  
Conan nodded a little, taking his spoon from his tea before blowing steam from it and setting it down. “The problem is,” he began. “I don’t know if I can trust you again…”  
Gwendolyn nodded. “I understand, but, um,” she fought back tears, her voice growing thick. “If you would just give me a chance, I-I will do anything in my power to show you how much I love you and,” she paused, covering her mouth. “I will do everything possible to never hurt you again.” Tears streamed down her face and she turned to the wall, wiping them away. She wanted to reach out and hold him, kiss him, bury herself in him and beg him to take her back but he still hadn’t even glanced at her.   
Conan leaned back in his chair, took a deep breath, and looked at the ceiling, glassy eyed. He exhaled slowly. “I want you to come back.”  
Gwendolyn suppressed a sob. “Th-thank you,” she reached out his hand, but he withdrew his.  
“I think I’m going to stay in the guest room for a couple of days,” he swallowed. “While we, um, talk things out.”   
Gwendolyn nodded, blinking. “Okay, okay.”  
“Alright then, I’ll…I’ll see you back there,” He stood up to leave and pushed in his chair, avoiding her gaze, but as he passed her he paused, placing his hand gently on her shoulder for a moment before walking out of the deli.  
Taking a moment to compose herself, Gwendolyn left and went back to the hotel, gathering her things and checking out. When she walked back in to the apartment Conan was sitting on the couch watching tv. She stood in the kitchen awkwardly.  
“You sure you want the guest room? I can go in there if you’d rather have the bedroom,” she said.  
Conan shook his head, staring at the television. “No, I’m already set up in there. It’s fine.”  
She nodded and brought her stuff into the bedroom. As she put her things away she noticed that everything was precisely where it had been a week ago. Her pillow askew at the same angle, the comforter folded back just so, and she realized he hadn’t been able to sleep in their bed during the week she’d been away. The thought made her ache. She wanted to rush into the living room, climb into his arms, smother him with kisses and tell him over and over how much she loved him, but it couldn’t be more clear that he wanted space.  
Hiding out in her office, she attempted to write for a while, not getting far and mostly sitting idly in front of her computer. Giving up, she took out a pad and her pencils, pulling up a picture of Conan online. She didn’t want to think about how sad it was that he was 20 feet away and instead she was staring at him on a screen, so instead she focused on the angle of his jaw, the curve of his cheekbones, his almost impossibly light eyebrows. A couple of hours passed before he was looking back at her from the paper. Trailing her fingers over his image, she looked at the clock, closed her computer, and set the drawing pad up on her easel.  
Creeping into the living room, she saw Conan was still sitting on the couch.  
“Are you hungry?” She asked softly.  
He shrugged. “Sure.”  
She nodded and went to the kitchen, peering in the fridge and the cupboards. Whipping together a quick pasta and salad, she meekly approached him and told him dinner was ready. They sat down together to eat, the only sound coming from their chewing and the clinking of forks.  
“It’s good,” Conan finally murmured halfway through.  
“Thank you,” she responded. “Glad you like it.” He still only looked down at his food, and when he finished he got up, cleaned off his plate, and set it in the rack to dry before returning to the couch. Gwendolyn finished her meal, cleaning up, and walked into the living room.  
“Can I…Could I join you?” She asked.  
He gave a non-committal shrug. Gwendolyn sat on the other side of the couch, folding one leg underneath herself. They sat there for an hour, silently. She wasn’t even sure what was on, she was focused on the waves of ice radiating off Conan that seemed impenetrable. It seemed that there should be some magical combination of words that would get him to speak to her again, to just look at her, but try as she might she couldn’t conjure them.   
“I’m going to bed,” he said flatly, placing the remote on her side of the couch and walking to the guest room, closing the door behind him. Staring at the door, her eyes grew watery. Only two inches of wood divided them but there was nothing she could do to cross it.  
Turning off the tv and heading to bed, she curled up in the blankets, weeping softly. _How do you make someone fall back in love with you?_  
——


	8. VIII

Gwendolyn woke early, but Conan had already left for work. He usually wasn’t gone by this time but it was clear he’d rather be anywhere else. Gwendolyn showered, and since the writing wasn’t coming to her, she set about deep-cleaning the apartment. Four hours later, her fingers pruny and everything smelling of lemons, surfaces sparkled but the cloud still rested over her heart. Deciding she needed to get out, she went to see a matinee, then did some shopping, grabbing some take-out on her way home from their favorite Chinese place.  
—-

Conan left so early he had to stall in a coffee shop for an hour because he wouldn’t have been able to get inside the studio. He couldn’t face another silent meal, and he didn’t know what to say because, frankly, he still wasn’t sure what he was feeling. The work day went alright, considering, and he was going to start inventing tasks to stay late when he stopped himself. The problem wasn’t going anywhere. No matter how early he came in, or how late he stayed, she would still be there waiting for him and he would have to deal with it.   
Hesitating before putting his key in the lock he took a breath, and went in. Not seeing her immediately he assumed she must be in her office, and decided it was time to stop hiding. Peering around the corner he saw only her empty chair, but before he could turn to check the bedroom something caught his eye. Conan turned on the light and walked in, looking at her easel. He recognized the picture immediately. It was taken for People magazine a few years back, and he knew the drawing hadn’t been there the day before. He realized she sat in here the night before, while he was staunchly ignoring her, and drew his face because it was the only way she could see his eyes looking back at her. A tear fell onto the paper, smearing his drawn chin.   
Then he heard her keys in the door and hurriedly replaced the pad, turning off the light and returning to the living room, wiping his face.  
Gwendolyn came in carrying a bag of take-out and two shopping bags.  
“Hello,” she said cautiously.  
“Hi,” he responded, trying to give at least half a smile.  
“I got Chinese food from Ming’s,” she held the bag aloft. “If you’re hungry.”  
“Yeah, yeah, that’d be great,” he said.   
She took down a couple of plates and they dished out their food.   
“So,” he asked awkwardly. “How was your day?”   
She stared at him for a moment before clearing her throat. “O-okay. Did some cleaning, then went to a movie. Then some shopping and came home. How was work?”   
Conan nodded. “Not bad. Patton Oswalt was on tonight, he’s always fun.”  
“Yeah, he’s great,” she said.  
They fell quiet again, eating.   
“So how’s Andy doing?” Gwendolyn asked after a couple of minutes. It was obvious to Conan she wanted to keep things going.   
“Pretty good I guess,” he said. “Nothing new.” His eyes met hers for the briefest second before returning to his plate.  
She nodded, heart beating fast. She wanted to ask more, but didn’t want to push him. They finished eating in silence and after cleaning up they each grabbed a book and sat on the couch, though neither of them focused particularly well.  
Around nine Conan shut his book and announced he was going to bed, once again retiring to the guest room and shutting the door. Gwendolyn went to the bedroom and laid down in the dark, not tired but unsure what else to do with herself, and eventually she fell asleep.  
Conan lay awake for a long time, passing things back and forth in his mind as he stared at the ceiling. Looking periodically over at the clock as it ticked past midnight, then one, then two, he finally sat up and stared through the darkness at the closed door.  
Prying it open, he crept across the silent apartment, hearing a far off siren and the jumble of the city rising from the streets. He stood in the doorway of their bedroom and saw her sleeping, her hair splayed out across the pillow and her hands twitching lightly. Standing there for a long time, he finally closed his eyes and took a deep breath, letting it out slowly before approaching the bed and pulling back the covers. He slid in, staying on his side, and Gwendolyn stirred gently but didn’t wake.   
The sound of her breathing soothed him, and he felt himself relax when she began to mumble in her sleep, as she often did. As per usual, it was mostly incoherent nonsense, but one word caught his ear.  
“ _Conan_.”  
Breathing hard, he gave in and scooted into her, pressing himself against her back and sliding his arm around her waist. Pressing his face into her hair, he breathed her in, and then felt her shake awake.   
For a moment she was unsure of what was going on, but then she turned around and saw his face staring back at hers, his eyes black in the moonlight. She twisted in bed, wrapping her arms around his neck and pressing her face to his chest, weeping. Tears fell from his eyes, landing like dew in her hair as they clung to one another.   
Once the tears were wiped away and their sniffling stopped, she turned around again, pressing her back into him and pulling his arm up to her chest. For the first time since their fight they both sank into a deep, restful sleep.  
——   


Waking the next morning, Gwendolyn turned and Conan’s eyes fluttered open. She looked at him, reaching a hand up to brush back his hair.  
“Good morning,” she said.  
“Morning.”  
“Could I kiss you?” She asked, rubbing his ear.   
He lifted his hand to her wrist. “I-I don’t think I’m there yet.”  
She nodded, looking down. “I understand,” she said. “Whenever you’re ready.”   
Conan rolled out of bed and started getting dressed for work. They had breakfast together and said goodbye. Gwendolyn spent the majority of the day writing and editing before starting dinner.  
Conan had a typical day at work. After lunch, Andy popped into his office.  
“How’s it going?” He asked.  
Conan shrugged, signing the document before him. “Not bad I suppose, you?”  
“Can’t complain, can’t complain,” Andy nodded. “You seem…better.”  
Conan looked up at him. “Yeah, well..” he cleared his throat. “Gwen came back and it’s…it’s early days, but we’re working on things.”  
“Ah, that’s good to hear,” Andy smiled at him. “Here’s hoping everything goes smoothly.”  
“Thank you,” Conan nodded.  
Andy said goodbye and gave a little wave. Conan went back to work, the rest of the day playing out as per usual before he went home.  
When Conan walked in Gwendolyn was standing over the stove, humming softly to herself.   
“Hey there,” she called as he walked in. “Chana Masala tonight.”  
“Mmm, yum,” he said, setting down his briefcase.   
“It’ll be about 20 minutes.”  
“Sounds good.”  
Conan decided to pick up his guitar and noodle around a bit. Sitting on the couch, he picked out a few songs, lost in the music for a moment before he noticed Gwendolyn staring at him.  
“What?” He asked, looking up at her.  
“Oh!” She looked surprised. “Nothing…” and she went back to stirring the pot.  
Returning to the guitar and picking out another song, it was a matter of minutes before he felt her eyes on him again. Looking out of the corner of his eye he saw she was looking at him while her arm absently stirred.  
“Okay, seriously, _what_ is it?”  
“I’m sorry,” she shook her head. “It’s just…I always think you’re so…sexy,” she paused. “When you play.”  
Conan swallowed. “Oh.” Looking down at the floor for a moment, he returned to the guitar and she returned to the meal.  
Gwendolyn could swear he chose a more impressive, intricate lick to play. His agile, long fingers dancing across the neck of the guitar as his other hand picked out the notes with dexterous precision. Taking care to watch without turning her head this time, she felt her face grow warm.  
“It’s ready,” she called out, taking down bowls and setting out the rice and curry on the table.  
They passed the evening amiably, and this time when they went to bed Conan followed her to the bedroom. They crawled under the covers together and held each other close, but as badly as she wanted them to, Conan’s lips did not touch her and his hands did not wander from her waist.   
Gwendolyn woke first the next morning. It was Saturday and Conan had the day off, but she had to get ready for a book reading and signing downtown. Turning over in bed she looked at Conan’s peaceful sleeping form and smiled. She couldn’t help but notice, however, the outline of his erection under the half-draped sheet across his torso. Her mouth filled with saliva and she felt a warm tingling between her thighs. She ached to reach out and take him in her hand, her mouth, but she knew she couldn’t, so she stared hungrily, like a woman dying of thirst before a wavering mirage.   
Tearing herself away, she jumped in the shower and as the water cascaded over her she worked her hand between her thighs, covering her mouth as she came to muffle her moans. Selecting a cherry-patterned dress and a cardigan, she applied her makeup and heard Conan stirring as she did the finishing touches. She was pulling on her shoes and checking her purse to make sure she had everything she needed when he entered the kitchen.   
“Good morning,” he said with a yawn.  
“Morning,” she responded. ‘I have a reading today, so I’ll be back later,” she pulled the door open and took half a step outside.   
“Hold on,” Conan stepped forward, grabbing her wrist.   
“What is it? I’m gonna be la—“  
He spun her toward him, taking her face in both hands and pressed his lips to hers, still for a moment before gently opening her mouth with his tongue and encircling hers, twisting his head to the side so they could drink each other deep.  
When he pulled away, Gwendolyn’s eyes remained closed. Until that moment she never knew what people meant when they said a kiss could make you ‘weak in the knees,’ but she found it difficult to stay upright.  
“Have a good day,” Conan murmured before letting go of her face.  
Gwendolyn just nodded, unable to form a sentence before Conan turned around and disappeared into the bedroom. She floated out of the door and onto the city street, light-headed and giddy.  
After the reading and book signing, Gwendolyn came back home to find Conan sitting on the couch, watching tv. They had a lunch of leftovers before sitting down to spend the afternoon reading. Then she made dinner and after sat down, returning to her book, but Conan lifted it out of her hands and set it on the table. Sitting next to her on the couch, he encircled one arm about her waist and used the other to cradle her head, leaning in to kiss her. Wrapping her arms about his neck, she sank into the kiss, lazily turning her head from side to side as their tongues melded together. They spent what seemed like hours just kissing, Conan’s hands never trailing beneath her shirt or skirt, like two teenagers who’d never been beyond first base. Gwendolyn noticed his growing erection pressing against his jeans and yearned to touch him, but kept her arms primly about his neck.  
When they finally parted, lips red and swollen, darkness had fallen and they were breathing hard. Heading to bed, they snuggled together chastely, and she didn’t know about Conan, but Gwendolyn’s dreams were filled with clothes-ripping passion that set her skin aflame.  
Gwendolyn awoke the next morning and immediately she felt Conan’s hard cock pressed against her ass. She could tell by his breathing that he was in a deep sleep, and she couldn’t help herself. Gently she inched herself backward, and began grinding into him, rubbing herself up and down against his persistent erection.   
For the briefest moment she felt him grinding back before he awoke with a snort.  
“Hey now…” he said, backing off and sitting up.  
“Sorry…”she muttered sheepishly, looking over her shoulder.  
He gave her a chiding glance but said nothing more, walking to the bathroom. His restraint was unfathomable to her. She assumed he must be getting off in the shower. After all, the only way she was getting through this torture was by pleasuring herself there and whenever he left for work. It crossed her mind to get naked, knock on the door and drop to her knees and beg. At this point she was running out of both patience and dignity. But she wanted to respect his boundaries, so instead as she heard him turn the water on, she quickly slid a hand between her legs, polishing herself off frantically before he returned.  
Conan left for work and his day went surprisingly well. They wrapped exceptionally early because they shot a remote segment the week before that they were using today, so Conan found himself getting home around four o’clock instead of his usual 6:30.  
Opening the door, he instantly heard moans and cries of passion issuing from the bedroom and alarms sounded in his head. _After everything?_ He thought. _She’s cheating in our home? In our BED?!_ His blood boiling, he tore through the apartment, rushing to the bedroom to confront them. Rounding the corner of the doorway what he saw stopped him cold.  
Gwendolyn was naked on the bed, eyes closed, one hand plunging a vibrator in and out of herself while the other vigorously rubbed her clit.   
“ _Fuck me, Conan, fuck, FUCK!”_ She gasped, body writhing wildly.  
Conan let out a surprised, “Oh!,” and her eyes flew open.  
“Oh, shit!” She squeaked, frantically scrambling to cover herself with the blanket, the vibrator clattering to the floor, buzzing comically against the floorboards before she reached down and snatched it up, turning it off and hiding it beneath the blanket.  
“I, um, I…you’re home…early,” she breathed heavily, cheeks flushed.  
Conan blinked. “Yeah, um,” he swallowed. “Filming, uh…” he swallowed again. “Yeah…”  
They stared at each other for a moment, unmoving. Then Gwendolyn, breathing hard, lowered the blankets, exposing her naked body. Conan stared at her, heart pounding, but still he did not move from the doorway. She watched him looking at her for a moment and then carefully she dragged her right hand across her thigh, replacing it between her legs, rubbing her clit as she kept his gaze, her eyelids growing heavy.  
“ _Conan_ ,” she breathed.  
He broke. With a sharp intake of breath, he pounced on the bed. Frantically they both tried to remove his clothes, but his pants were still around his knees when he entered her. Within five strokes she was already twitching, gripping his cock from the inside as an orgasm rocked through her. Working his thumb against her clit, he couldn’t tell where one orgasm ended and the other began as she gasped and seized, barely able to get out the first syllable of his name as she cried out. Conan wanted to make it last but the intensity overwhelmed him and he came, hammering deep inside her with his last few irregular strokes. She wrapped her legs around him, holding him inside and he could still feel her body fluttering around him.  
“S-so g-good,” she gasped, petting his hair.  
He nodded into her neck. “Yeah.”  
“I m-missed you s-so much.”  
“Me too,” Conan laughed.  
“What’s f-funny?” Gwendolyn asked, slowly catching her breath and unwinding her legs so he could roll away.  
“It’s just,” he chuckled. “I never thought I’d fuck a woman so hard she’d develop a stutter.” He held his chest and laughed. Gwendolyn joined him, her breath still hitching from time to time, which only made them laugh harder. They spent the rest of the evening enjoyably, falling asleep, finally sated.  
Waking the next morning to the alarm, Gwendolyn once again turned over to see Conan was hard. Putting her hand on his thigh, she stopped him before he got out of bed.  
“Could I…could I, you know…” she flicked her eyes down to his lap then looked back at his face.  
“I don’t know to what you’re referring,” Conan feigned ignorance in a high-society accent. Gwendolyn smiled. She knew sometimes he liked to hear the words.  
Leaning in, brushing her lips against his ear she asked in a low, throaty whisper. “ _Can I suck your cock and will you please cum in my hot, tight throat?”_  
She saw a shiver run through him.  
“ _Yes_ ,” he answered, sitting back on the bed. She pulled down his pajama bottoms, revealing his stiff cock and began lovingly stroking it, gently caressing it with her face, her lips, before kissing it from base to tip. Without warning, she sank the entirety of his length down her throat. He let out a high-pitched moan and arched his back. Sticking out her tongue and licking the top of his balls, she sucked hard as she pulled up, hollowing her cheeks and focusing on the tip. Using her hand to firmly stroke him, she created a seal with her mouth, swirling and sucking while her other hand cradled and rubbed his balls. His fingers wound into her hair, encouraging her to increase her speed and his hips thrust forward into her mouth. She hummed and moaned around his cock, taking him as deep as she could, lips sliding rapidly along his shaft. Conan called out her name, rocking shamelessly as he shot into the back of her throat, cock throbbing as it pulsed out every last drop.  
Gwendolyn pulled off and Conan covered his eyes, breathing hard.  
“Damn, I missed that,” he pulled up his pajama bottoms.  
Gwendolyn smiled. “Me too. Waking up to you hard every day this past week and not being able to do anything about it? Torture,” she chuckled.  
“Yeah, it was rough,” he said. “I just wasn’t…you know, ready,”  
“Oh, I’m sorry,” Gwendolyn said quickly. “I don’t want you to think I was complaining. I’m just grateful to be back where we are.”  
Conan nodded. “Yeah, I was surprised how accustomed to sex I’d become,” he chuckled. “A couple of weeks without and I was rubbing myself raw.”  
“I knew you had to be dealing somehow,” Gwendolyn smiled. “I practically gave myself carpal tunnel,” she rotated her wrist for effect.  
He laughed. “Yeah, my internet search history is probably horrifying,” he ran a hand over his brow. “I tried for a while to use my imagination, but every time I did,” he flicked his eyes up toward hers. “You were there. And it hurt,” Gwendolyn got quiet, reaching over to take his hand. “And even with the porn, I eventually found myself searching for women who looked like you. I couldn’t help it.” Gwendolyn took his face in her hands and kissed him.   
—-  


They spent the next couple of weeks gradually returning to their previous routine, though something shifted. There was a depth, new roots sunk into fresh soil, anchoring them to the future.   
One morning when they were brushing their teeth, Gwendolyn bent over to spit and rinse, wiping her mouth, when Conan casually and quietly placed the ring on the counter next to her basin.  
Whipping her head to look at him, he stared forward into the mirror, brushing his teeth.  
“Really?” She managed to choke out.  
Conan spit, rinsed, and wiped his mouth before turning to her. “Unless you’ve already made plans for April 11th…” he replied calmly.  
Gwendolyn threw herself into his arms, crying and kissing him, and he held her near, swaying gently back and forth. They parted and Gwendolyn returned the ring to her finger, turning it to catch the light.  
Leaning in to kiss him again, she whispered, “I love you, Conan.”  
“I love you, too,” he replied.   
——  


November rolled around and Gwendolyn was making beef stew to combat a particularly chilly day when Conan came home from work, slamming the door behind him. He strode to the living room, pacing back and forth a couple of times, fuming, before sitting with his hands balled into fists. Taking a deep breath he lowered his face into his hands, breathing into them.   
Gwendolyn was frozen, spoon hovering over the stew pot. Turning down the burner to a simmer, she tiptoed to the living room.  
“Conan…” she kept her voice low and soft. “What’s wrong?”  
He dragged his hands down his face, laying back on the couch, staring at the ceiling.  
“Bill was on the show today…” he murmured, sniffing a little.  
“Oh…” Gwendolyn said in a small voice.  
“I went to see him before the show, and I was okay,” Conan said. She could see him grinding his teeth. “I even made it through the interview alright. Talking…laughing…” His nose flared. “But when I went backstage after the show, he opened the door…and I punched him in the fucking face.”  
Gwendolyn gasped, covering her face. They were quiet for a moment, Conan still staring upward.  
“Did it…Did it make you feel better?” Gwendolyn decided to risk asking.  
Conan looked over at her, sat up, and shook his head. “No, no, it didn’t. He just…took it. And then he said he deserved it and apologized to me,” he shook his head again. “I don’t know. I just feel sick.”  
Gwendolyn nodded. She disappeared to the kitchen for a second, returning to join Conan on the couch with a bag of frozen corn which she applied to the knuckles of his right hand.   
“I’m sorry,” she whispered, kissing his cheek. “I’m sorry on top of everything, you lost a friend in all this.”  
Conan nodded. “Thank you,” he kissed the top of her head. “You know Bill said something as he was leaving,” he looked at the floor. “He said, ‘Conan, I hope you know how lucky you are’.”  
Gwendolyn looked away sheepishly. Then she cleared her throat. “I’m the lucky one,” she ran her fingers through his hair.   
——

  
As Fall slipped into Winter and the holidays approached, Gwendolyn found herself busy with the initial stages of wedding planning. She was fortunate enough to find a dress at the first shop she tried, and by mid-December it was in alterations. Juggling notes on the draft of her third book kept her almost constantly busy, but she was happier than she could remember being in her life.  
For Conan’s part, things were equally hectic. The time was soon approaching for him to leave Late Night and take over The Tonight Show. The pressure of an impending wedding, a new show - not to mention moving across the country – was a lot for the two of them to handle, but they took it in stride and tackled each problem as it arose.  
One day in January, Gwendolyn bundled up tight, a basket bearing roast chicken and winter squash tucked under one coat-puffed arm. Gasping as the frigid air slapped her face, she attempted to pull her scarf more securely about her face as she hailed a cab to Rockefeller Plaza.   
Stepping into the lobby was like entering a sauna and immediately she unzipped her coat and unwound her scarf, pulling off a glove with her teeth as she tried to reach the elevator button with her basket-laden arm. She wasn’t paying attention to the slowly closing door when someone suddenly slid in just before they shut.  
“Hey,” he panted.   
Gwendolyn looked up, eyes going wide and nearly dropping her basket. “Bill!” She supposed it was foolish to think she’d never run into him, considering he worked just a few floors up, but up until now she’d been lucky.  
“How are you?” He asked.   
“I’m…Bill, you can’t be here…” she looked nervously to the door, then flicked her eyes up to the ascending numbers. If she reached the sixth floor and Conan was perchance standing on the other side of those doors…  
“I know, I know…” Bill nodded. He reached over and pressed the button for the fifth floor, then the emergency stop. “I’ll get off early and walk up to eight. I just wanted to talk to you for a minute.”  
Gwendolyn nodded, nervous. Her eyes darted about the restricted space. Not wanting to look directly at him, she wanted to back into the corner. At the same time she couldn’t help but notice the pleasant notes of bergamot and tangerine wafting off his skin.  
“I just…” he held out his hands, gesturing as if trying to grasp words in the air. “I know you’re leaving soon and…and I feel like I need to apologize,” he let his arms drop. Gwendolyn allowed herself to look at him and saw his Adam’s apple bob up and down as he swallowed hard. “I don’t really know what to say, but I’m just sorry.”  
She looked at him, his expression soft. “Me too, Bill. After all, it’s not like it was all you…”  
Bill looked at her meaningfully, paused. “It wasn’t?”   
Their eyes met and Gwendolyn felt a finger of ice slide down her spine as those dark blue eyes met her own with desperate questioning.   
She clenched her left fist, thumb grazing her ring, and cleared her throat, reaching out to push the button that resumed the elevator. “Past tense.”  
Bill looked away from her and nodded. “Well, um…good luck with California and you know…everything,” he said, eyes lingering on her ring.  
“Thank you, Bill. You too.”  
When the door opened on the fifth floor he took a step and half raised his arm as though he were going to reach out to touch her one last time, but apparently thought better of it and turned it into a half wave. They murmured a quiet goodbye and as the silver doors shut in front of her Gwendolyn let out a breath she wasn’t aware she’d been holding.


	9. IX

The day arrived. Conan’s final _Late Night_ show. Gwendolyn went in to work with him that day. The mood on the floor was equal parts somber and celebratory, like the last day of senior year among a particular tight group of friends. People reminisced about the early days, fighting to stay on the air and three a.m. Chinese food runs, silly stories were told and it was a mixture of laughter and tears.  
Gwendolyn sat in the audience, and after the guests and The White Stripes, she watched Conan deliver his final speech in his sharp black suit behind the familiar desk for the last time. As he spoke and his voice began to break, tears threatening his eyes, they streamed down her own face and her heart swelled with pride for this beautiful, brilliant man.   
The cameras switched off and the audience spent a long time giving Conan yet another standing ovation. He was obviously feeling overwhelmed and did his best to express his gratitude, but he knew there were no words that could convey how much each person who helped him get where he was at that moment meant to him.   
When the audience filed out, Gwendolyn walked up and embraced him. They swayed gently back and forth on the set, ignoring the crew bustling about.   
“I am so proud of you,” she whispered into his ear.  
Conan could only nod. He feared that if he tried to speak his voice would come out broken. They parted and she walked him wet-eyed backstage to his dressing room. He removed his make-up and changed into jeans, a Guinness t-shirt, and an aviator jacket. He sat down on the couch next to Gwendolyn for a moment. The party would be starting soon, and though Conan was excited to gather with everyone and celebrate the last 16+ years of comedy, sweat, and tears, there was also a part of him that very much wanted to be alone to quietly reflect on the mass of feelings roiling in his chest.  
“You okay?” Gwendolyn asked, carding her fingers through his soft red hair before trailing them over the prominent freckles on the back of his neck.  
Conan opened his mouth. Closed it. Opened it again. “I guess…I guess I don’t know. I feel…too many things.”  
Gwendolyn just nodded, wrapping her arms around him. He buried his face in the crook of her neck, lowering himself and pulling in close to her body, tears beginning to trail down his face and stain the collar of her dress.  
“Tighter,” he whispered. Gwendolyn drew her arms closer together.   
“ _Tighter_.” She obliged and Conan curled himself into her, tears silently falling. She gently petted his hair, and he was lulled by the rise and fall of her chest as she breathed. After a few minutes, Conan unraveled himself. He sat up straight, took one deep breath and exhaled slowly, wiping his eyes.  
“Okay,” he nodded. “Let’s go.” Conan took Gwendolyn by the hand and they made their way to the festivities.  
———  
  
A week later, basically everything was packed. Gwendolyn looked around the bare apartment as she finished packing the living room. Though they hadn’t been there long, it had been a happy place and she would remember it fondly.  
“Do we have more bubble wrap?” Conan asked, appearing around the corner lugging a particularly heavy box. The muscles in his arms stood out alluringly and Gwendolyn noticed a tiny sweat circle on the back of his shirt as he passed her by.  
“Yeah, I think there’s one roll left in the kitchen maybe.” Her voice echoed oddly off of the bare walls. Conan set down the open-flapped box and did a half jog to the kitchen, scooping up the bubble wrap and using it to cover a bust of Teddy Roosevelt. They finished gathering the last of their belongings over the next hour or so, leaving out only the necessities they would need for the night. The movers were coming bright and early, and then it was off to the airport.   
When they were done they looked around at the stacked boxes, sweaty and panting.   
“Well, that’s that,” Conan said.  
Gwendolyn nodded. “Do you want to order some delivery?”  
“Yeah,” Conan said. “Wanna just do a pizza since we don’t really have plates or anything?”  
“Good plan.”  
“Okay, I’ll call.”  
Gwendolyn nodded. “Thanks, I’m going to jump in the shower.”  
After Gwendolyn emerged and she and Conan swapped, her waiting for the pizza while he showered. They ate their pizza over the box like broke college students and afterwards collapsed into bed, muscles sore from a day filled with bending and lifting.   
Conan turned toward Gwendolyn, reaching over to graze her arm. “So,” he murmured. “One last time? To say goodbye to the place?” She smiled, nodding and dragging herself to him. Conan snaked a hand underneath her tank top, cupping and massaging her breast as their lips met and their tongues twisted together. She threw a leg over him, and he rolled on top, notching himself between her legs. Languidly they allowed their hands to roam over one another, not removing their clothes just yet, but enjoying the pressure and tingle of fingertips as they explored. Conan’s cock grew hard and he dug himself into her, feeling the heat radiating from between her thighs as she ground herself forward.  
“Mmmm,” she purred. “You know, I could cum just from this.”  
“Oh yeah?” Conan said.   
Gwendolyn nodded against his lips. “Yeah, I love it.”  
“ _Oh, you like it when I rub my cock against you?_ ” Conan said. His voice sank lower than usual and it sent shivers through her.  
“Yeah, honey, I love it.”  
Conan pulled off her shorts and stood up briefly to step out of his sweatpants before coming back to the bed and positioning himself over her. He leaned on one arm and with the other hand he used the tip of his cock to rub up and down against her opening, causing Gwendolyn to mewl gently.  
“You like that?” He breathed, voice gruff.  
“Yeah,” Gwendolyn panted.  
“Yeah, _what_?” Conan insisted, pulling away for a minute to deny her stimulation.  
_“I love it. I love your big cock_ ,” she whined. Conan resumed rubbing her clit faster and faster with the head of his cock, and she grew slippery beneath him as she squirmed.  
“Oh Conan, _please_ fuck me, _fuck me_ ,” she begged. He teased her for another minute or so before he acquiesced and slid inside, lowering himself so their faces were close together.  
“Is this what you want?” Conan growled, pounding into her, fingers of his right hand working on her clit.   
“ _Yes, fuck yes, you fuck me so good baby, yes_ ,” she moaned.  
Conan tilted his hips forward, knowing he hit the right spot when her eyes rolled back and her screams turned wordless. _“I love fucking you_ ,” he panted before his own movements lost their control and he thrust forth, coming hard before collapsing.  
He stayed inside her while they held one another until their breathing returned to normal, finally rolling over to his side of the bed when he felt his eyes beginning to droop.   
“Love you,” Gwendolyn whispered, leaning over to give one last soft kiss.  
“Love you, too.” Conan said. And as the moon rose over their last night in New York City, they fell asleep grateful for the first bed, the first home, they’d shared.  
—-

The next day, as the plane was filling up, Conan and Gwendolyn adjusted themselves in their seats. The slightly muffled announcements came over the speaker and then they took off. Conan looked out the window, the buildings of New York growing smaller and smaller. He thought about all that lay behind him these past 46 years, and all the unknowns and adventures that lay ahead as the country whipped by below him.  
“You okay, hun?” Gwendolyn asked, reaching over to squeeze his hand.   
Conan turned to her, smiled. “Yeah, great.” He intertwined their fingers and lifted her hand to his mouth, brushing it with a kiss. “Just great.” Side by side they raced forth, unsure of what the future what might hold, but certain they would face it together.

  
The End  


**Notes for the Chapter:**

> Thank you to anyone who has taken the time to read or leave kudos. I really appreciate it!


End file.
